diff --git a/doc/getting_started/troubleshooting/deploy_hf_model_aml.ipynb b/doc/getting_started/troubleshooting/deploy_hf_model_aml.ipynb
index 2b5600ce5a..971a066c83 100644
--- a/doc/getting_started/troubleshooting/deploy_hf_model_aml.ipynb
+++ b/doc/getting_started/troubleshooting/deploy_hf_model_aml.ipynb
@@ -128,14 +128,12 @@
    "metadata": {},
    "outputs": [],
    "source": [
-    "from typing import Union\n",
-    "\n",
     "from azure.ai.ml import MLClient\n",
     "from azure.core.exceptions import ResourceNotFoundError\n",
     "from azure.identity import DefaultAzureCredential, InteractiveBrowserCredential\n",
     "\n",
     "try:\n",
-    "    credential: Union[DefaultAzureCredential, InteractiveBrowserCredential] = DefaultAzureCredential()\n",
+    "    credential: DefaultAzureCredential | InteractiveBrowserCredential = DefaultAzureCredential()\n",
     "    credential.get_token(\"https://management.azure.com/.default\")\n",
     "except Exception as ex:\n",
     "    credential = InteractiveBrowserCredential()\n",
diff --git a/doc/getting_started/troubleshooting/deploy_hf_model_aml.py b/doc/getting_started/troubleshooting/deploy_hf_model_aml.py
index b55a818a6c..b6fa4a1e67 100644
--- a/doc/getting_started/troubleshooting/deploy_hf_model_aml.py
+++ b/doc/getting_started/troubleshooting/deploy_hf_model_aml.py
@@ -106,14 +106,13 @@
 # Set up the `DefaultAzureCredential` for seamless authentication with Azure services. This method should handle most authentication scenarios. If you encounter issues, refer to the [Azure Identity documentation](https://docs.microsoft.com/en-us/python/api/azure-identity/azure.identity?view=azure-python) for alternative credentials.
 #
 # %%
-from typing import Union
 
 from azure.ai.ml import MLClient
 from azure.core.exceptions import ResourceNotFoundError
 from azure.identity import DefaultAzureCredential, InteractiveBrowserCredential
 
 try:
-    credential: Union[DefaultAzureCredential, InteractiveBrowserCredential] = DefaultAzureCredential()
+    credential: DefaultAzureCredential | InteractiveBrowserCredential = DefaultAzureCredential()
     credential.get_token("https://management.azure.com/.default")
 except Exception as ex:
     credential = InteractiveBrowserCredential()
diff --git a/doc/getting_started/troubleshooting/download_and_register_hf_model_aml.ipynb b/doc/getting_started/troubleshooting/download_and_register_hf_model_aml.ipynb
index 29e7fdec00..65cb1229a3 100644
--- a/doc/getting_started/troubleshooting/download_and_register_hf_model_aml.ipynb
+++ b/doc/getting_started/troubleshooting/download_and_register_hf_model_aml.ipynb
@@ -71,7 +71,6 @@
    "source": [
     "# Import the Azure ML SDK components required for workspace connection and model management.\n",
     "import os\n",
-    "from typing import Union\n",
     "\n",
     "# Import necessary libraries for Azure ML operations and authentication\n",
     "from azure.ai.ml import MLClient, UserIdentityConfiguration\n",
@@ -201,7 +200,7 @@
    "source": [
     "# Setup Azure credentials, preferring DefaultAzureCredential and falling back to InteractiveBrowserCredential if necessary\n",
     "try:\n",
-    "    credential: Union[DefaultAzureCredential, InteractiveBrowserCredential] = DefaultAzureCredential()\n",
+    "    credential: DefaultAzureCredential | InteractiveBrowserCredential = DefaultAzureCredential()\n",
     "    # Verify if the default credential can fetch a token successfully\n",
     "    credential.get_token(\"https://management.azure.com/.default\")\n",
     "except Exception as ex:\n",
diff --git a/doc/getting_started/troubleshooting/download_and_register_hf_model_aml.py b/doc/getting_started/troubleshooting/download_and_register_hf_model_aml.py
index 34013c449f..251e49ecf2 100644
--- a/doc/getting_started/troubleshooting/download_and_register_hf_model_aml.py
+++ b/doc/getting_started/troubleshooting/download_and_register_hf_model_aml.py
@@ -61,7 +61,6 @@
 # %%
 # Import the Azure ML SDK components required for workspace connection and model management.
 import os
-from typing import Union
 
 # Import necessary libraries for Azure ML operations and authentication
 from azure.ai.ml import MLClient, UserIdentityConfiguration
@@ -160,7 +159,7 @@
 # %%
 # Setup Azure credentials, preferring DefaultAzureCredential and falling back to InteractiveBrowserCredential if necessary
 try:
-    credential: Union[DefaultAzureCredential, InteractiveBrowserCredential] = DefaultAzureCredential()
+    credential: DefaultAzureCredential | InteractiveBrowserCredential = DefaultAzureCredential()
     # Verify if the default credential can fetch a token successfully
     credential.get_token("https://management.azure.com/.default")
 except Exception as ex:
diff --git a/pyproject.toml b/pyproject.toml
index ee6ef1b728..243d636931 100644
--- a/pyproject.toml
+++ b/pyproject.toml
@@ -341,8 +341,6 @@ ignore = [
     "DOC502",  # Raised exception is not explicitly raised
     "PERF203",  # try-except-in-loop (intentional per-item error handling)
     "SIM117",  # multiple-with-statements (combining often exceeds line length)
-    "UP007",  # non-pep604-annotation-union (keep Union[X, Y] syntax)
-    "UP045",  # non-pep604-annotation-optional (keep Optional[X] syntax)
 ]
 extend-select = [
     "D204",  # 1 blank line required after class docstring
diff --git a/pyrit/analytics/result_analysis.py b/pyrit/analytics/result_analysis.py
index 9e158ed88a..2083bb720f 100644
--- a/pyrit/analytics/result_analysis.py
+++ b/pyrit/analytics/result_analysis.py
@@ -4,7 +4,7 @@
 from collections import defaultdict
 from collections.abc import Sequence
 from dataclasses import dataclass
-from typing import TYPE_CHECKING, Optional
+from typing import TYPE_CHECKING
 
 from pyrit.models import (
     AttackOutcome,
@@ -22,7 +22,7 @@
 class AttackStats:
     """Statistics for attack analysis results."""
 
-    success_rate: Optional[float]
+    success_rate: float | None
     total_decided: int
     successes: int
     failures: int
@@ -118,7 +118,7 @@ def get_cached_results_for_technique(
     *,
     technique_eval_hash: str,
     objective_target_eval_hash: str,
-    additional_filters: Optional[Sequence[IdentifierFilter]] = None,
+    additional_filters: Sequence[IdentifierFilter] | None = None,
 ) -> list[AttackResult]:
     """
     Return cached AttackResults matching a (technique × objective target) pair.
@@ -170,7 +170,7 @@ def get_cached_results_for_technique(
     return matches
 
 
-def _objective_target_eval_hash_for(attack_result: AttackResult) -> Optional[str]:
+def _objective_target_eval_hash_for(attack_result: AttackResult) -> str | None:
     """
     Return the ObjectiveTargetEvaluationIdentifier eval hash for a result.
 
diff --git a/pyrit/auth/azure_auth.py b/pyrit/auth/azure_auth.py
index 06e2ff1ade..647f05f7c8 100644
--- a/pyrit/auth/azure_auth.py
+++ b/pyrit/auth/azure_auth.py
@@ -6,7 +6,7 @@
 import inspect
 import logging
 import time
-from typing import TYPE_CHECKING, Any, Union, cast
+from typing import TYPE_CHECKING, Any, cast
 
 import msal
 from azure.core.credentials import AccessToken
@@ -41,7 +41,7 @@ class TokenProviderCredential:
     get_azure_token_provider) and Azure SDK clients that require a TokenCredential object.
     """
 
-    def __init__(self, token_provider: Callable[[], Union[str, Callable[..., Any]]]) -> None:
+    def __init__(self, token_provider: Callable[[], str | Callable[..., Any]]) -> None:
         """
         Initialize TokenProviderCredential.
 
@@ -75,7 +75,7 @@ class AsyncTokenProviderCredential:
     async clients that require an AsyncTokenCredential object (with async def get_token).
     """
 
-    def __init__(self, token_provider: Callable[[], Union[str, Awaitable[str]]]) -> None:
+    def __init__(self, token_provider: Callable[[], str | Awaitable[str]]) -> None:
         """
         Initialize AsyncTokenProviderCredential.
 
@@ -394,7 +394,7 @@ def get_azure_openai_auth(endpoint: str) -> Callable[[], Awaitable[str]]:
     return get_azure_async_token_provider(scope)
 
 
-def get_speech_config(resource_id: Union[str, None], key: Union[str, None], region: str) -> speechsdk.SpeechConfig:
+def get_speech_config(resource_id: str | None, key: str | None, region: str) -> speechsdk.SpeechConfig:
     """
     Get the speech config using key/region pair (for key auth scenarios) or resource_id/region pair
     (for Entra auth scenarios).
@@ -436,8 +436,8 @@ def get_speech_config(resource_id: Union[str, None], key: Union[str, None], regi
 async def get_speech_config_async(
     *,
     token_provider: Callable[[], str | Awaitable[str]] | None,
-    resource_id: Union[str, None],
-    key: Union[str, None],
+    resource_id: str | None,
+    key: str | None,
     region: str,
 ) -> speechsdk.SpeechConfig:
     """
diff --git a/pyrit/auth/copilot_authenticator.py b/pyrit/auth/copilot_authenticator.py
index a069af33ff..434dff4fbe 100644
--- a/pyrit/auth/copilot_authenticator.py
+++ b/pyrit/auth/copilot_authenticator.py
@@ -7,7 +7,7 @@
 import os
 import sys
 from datetime import datetime, timedelta, timezone
-from typing import Any, Optional
+from typing import Any
 
 from msal_extensions import FilePersistence, build_encrypted_persistence
 
@@ -196,7 +196,7 @@ def _create_persistent_cache(cache_file: str, fallback_to_plaintext: bool = Fals
             logger.error(f"Encryption unavailable ({e}) and fallback_to_plaintext is False. Cannot proceed.")
             raise
 
-    async def _get_cached_token_if_available_and_valid_async(self) -> Optional[dict[str, Any]]:
+    async def _get_cached_token_if_available_and_valid_async(self) -> dict[str, Any] | None:
         """
         Retrieve and validate cached token.
 
@@ -258,7 +258,7 @@ async def _get_cached_token_if_available_and_valid_async(self) -> Optional[dict[
                 logger.error(f"Failed to load cached token ({error_name}): {e}")
             return None
 
-    def _save_token_to_cache(self, *, token: str, expires_in: Optional[int] = None) -> None:
+    def _save_token_to_cache(self, *, token: str, expires_in: int | None = None) -> None:
         """
         Save token to persistent cache with metadata.
 
@@ -301,7 +301,7 @@ def _clear_token_cache(self) -> None:
         except Exception as e:
             logger.error(f"Failed to clear cache: {e}")
 
-    async def _fetch_access_token_with_playwright_async(self) -> Optional[str]:
+    async def _fetch_access_token_with_playwright_async(self) -> str | None:
         """
         Fetch access token using Playwright browser automation.
 
@@ -339,7 +339,7 @@ async def _fetch_access_token_with_playwright_async(self) -> Optional[str]:
         # If not on Windows or using the right loop already, proceed normally
         return await self._run_playwright_browser_automation_async()
 
-    async def _run_playwright_in_thread_async(self) -> Optional[str]:
+    async def _run_playwright_in_thread_async(self) -> str | None:
         """
         Run Playwright browser automation in a separate thread with ProactorEventLoop.
         This is needed on Windows when the main loop is SelectorEventLoop (e.g., in Jupyter).
@@ -348,21 +348,21 @@ async def _run_playwright_in_thread_async(self) -> Optional[str]:
             Optional[str]: The bearer token if successfully retrieved, None otherwise.
         """
 
-        def run_in_new_loop() -> Optional[str]:
+        def run_in_new_loop() -> str | None:
             if sys.platform == "win32":
                 new_loop = asyncio.ProactorEventLoop()
             else:
                 new_loop = asyncio.new_event_loop()
             asyncio.set_event_loop(new_loop)
             try:
-                result: Optional[str] = new_loop.run_until_complete(self._run_playwright_browser_automation_async())
+                result: str | None = new_loop.run_until_complete(self._run_playwright_browser_automation_async())
                 return result
             finally:
                 new_loop.close()
 
         return await asyncio.get_running_loop().run_in_executor(None, run_in_new_loop)
 
-    async def _run_playwright_browser_automation_async(self) -> Optional[str]:
+    async def _run_playwright_browser_automation_async(self) -> str | None:
         """
         Execute the actual Playwright browser automation to fetch the access token.
 
diff --git a/pyrit/auth/manual_copilot_authenticator.py b/pyrit/auth/manual_copilot_authenticator.py
index b175118878..24bf9da2e7 100644
--- a/pyrit/auth/manual_copilot_authenticator.py
+++ b/pyrit/auth/manual_copilot_authenticator.py
@@ -3,7 +3,7 @@
 
 import logging
 import os
-from typing import Any, Optional
+from typing import Any
 
 import jwt
 
@@ -36,7 +36,7 @@ class ManualCopilotAuthenticator(Authenticator):
     #: Environment variable name for the Copilot access token
     ACCESS_TOKEN_ENV_VAR: str = "COPILOT_ACCESS_TOKEN"
 
-    def __init__(self, *, access_token: Optional[str] = None) -> None:
+    def __init__(self, *, access_token: str | None = None) -> None:
         """
         Initialize the ManualCopilotAuthenticator with a pre-obtained access token.
 
diff --git a/pyrit/auxiliary_attacks/gcg/attack/base/attack_manager.py b/pyrit/auxiliary_attacks/gcg/attack/base/attack_manager.py
index 787154fe75..c1e898343b 100644
--- a/pyrit/auxiliary_attacks/gcg/attack/base/attack_manager.py
+++ b/pyrit/auxiliary_attacks/gcg/attack/base/attack_manager.py
@@ -10,7 +10,7 @@
 import random
 import time
 from copy import deepcopy
-from typing import Any, Optional
+from typing import Any
 
 import numpy as np
 import pandas as pd
@@ -132,7 +132,7 @@ def __init__(
         target: str,
         tokenizer: Any,
         control_init: str = "! ! ! ! ! ! ! ! ! ! ! ! ! ! ! ! ! ! ! !",
-        test_prefixes: Optional[list[str]] = None,
+        test_prefixes: list[str] | None = None,
     ) -> None:
         """
         Initializes the AttackPrompt object with the provided parameters.
@@ -417,8 +417,8 @@ def __init__(
         targets: list[str],
         tokenizer: Any,
         control_init: str = "! ! ! ! ! ! ! ! ! ! ! ! ! ! ! ! ! ! ! !",
-        test_prefixes: Optional[list[str]] = None,
-        managers: Optional[dict[str, type[AttackPrompt]]] = None,
+        test_prefixes: list[str] | None = None,
+        managers: dict[str, type[AttackPrompt]] | None = None,
     ) -> None:
         """
         Initializes the PromptManager object with the provided parameters.
@@ -539,12 +539,12 @@ def __init__(
         targets: list[str],
         workers: list[ModelWorker],
         control_init: str = "! ! ! ! ! ! ! ! ! ! ! ! ! ! ! ! ! ! ! !",
-        test_prefixes: Optional[list[str]] = None,
-        logfile: Optional[str] = None,
-        managers: Optional[dict[str, Any]] = None,
-        test_goals: Optional[list[str]] = None,
-        test_targets: Optional[list[str]] = None,
-        test_workers: Optional[list[ModelWorker]] = None,
+        test_prefixes: list[str] | None = None,
+        logfile: str | None = None,
+        managers: dict[str, Any] | None = None,
+        test_goals: list[str] | None = None,
+        test_targets: list[str] | None = None,
+        test_workers: list[ModelWorker] | None = None,
     ) -> None:
         """
         Initializes the MultiPromptAttack object with the provided parameters.
@@ -619,7 +619,7 @@ def get_filtered_cands(
         worker_index: int,
         control_cand: torch.Tensor,
         filter_cand: bool = True,
-        curr_control: Optional[str] = None,
+        curr_control: str | None = None,
     ) -> list[str]:
         cands, count = [], 0
         worker = self.workers[worker_index]
@@ -656,8 +656,8 @@ def run(
         topk: int = 256,
         temp: float = 1.0,
         allow_non_ascii: bool = True,
-        target_weight: Optional[float] = None,
-        control_weight: Optional[float] = None,
+        target_weight: float | None = None,
+        control_weight: float | None = None,
         anneal: bool = True,
         anneal_from: int = 0,
         prev_loss: float = np.inf,
@@ -873,12 +873,12 @@ def __init__(
         progressive_goals: bool = True,
         progressive_models: bool = True,
         control_init: str = "! ! ! ! ! ! ! ! ! ! ! ! ! ! ! ! ! ! ! !",
-        test_prefixes: Optional[list[str]] = None,
-        logfile: Optional[str] = None,
-        managers: Optional[dict[str, Any]] = None,
-        test_goals: Optional[list[str]] = None,
-        test_targets: Optional[list[str]] = None,
-        test_workers: Optional[list[ModelWorker]] = None,
+        test_prefixes: list[str] | None = None,
+        logfile: str | None = None,
+        managers: dict[str, Any] | None = None,
+        test_goals: list[str] | None = None,
+        test_targets: list[str] | None = None,
+        test_workers: list[ModelWorker] | None = None,
         **kwargs: Any,
     ) -> None:
         """
@@ -986,8 +986,8 @@ def run(
         topk: int = 256,
         temp: float = 1.0,
         allow_non_ascii: bool = False,
-        target_weight: Optional[float] = None,
-        control_weight: Optional[float] = None,
+        target_weight: float | None = None,
+        control_weight: float | None = None,
         anneal: bool = True,
         test_steps: int = 50,
         incr_control: bool = True,
@@ -1119,12 +1119,12 @@ def __init__(
         targets: list[str],
         workers: list[ModelWorker],
         control_init: str = "! ! ! ! ! ! ! ! ! ! ! ! ! ! ! ! ! ! ! !",
-        test_prefixes: Optional[list[str]] = None,
-        logfile: Optional[str] = None,
-        managers: Optional[dict[str, Any]] = None,
-        test_goals: Optional[list[str]] = None,
-        test_targets: Optional[list[str]] = None,
-        test_workers: Optional[list[ModelWorker]] = None,
+        test_prefixes: list[str] | None = None,
+        logfile: str | None = None,
+        managers: dict[str, Any] | None = None,
+        test_goals: list[str] | None = None,
+        test_targets: list[str] | None = None,
+        test_workers: list[ModelWorker] | None = None,
         **kwargs: Any,
     ) -> None:
         """
@@ -1225,8 +1225,8 @@ def run(
         topk: int = 256,
         temp: float = 1.0,
         allow_non_ascii: bool = True,
-        target_weight: Optional[float] = None,
-        control_weight: Optional[float] = None,
+        target_weight: float | None = None,
+        control_weight: float | None = None,
         anneal: bool = True,
         test_steps: int = 50,
         incr_control: bool = True,
@@ -1331,12 +1331,12 @@ def __init__(
         targets: list[str],
         workers: list[ModelWorker],
         control_init: str = "! ! ! ! ! ! ! ! ! ! ! ! ! ! ! ! ! ! ! !",
-        test_prefixes: Optional[list[str]] = None,
-        logfile: Optional[str] = None,
-        managers: Optional[dict[str, Any]] = None,
-        test_goals: Optional[list[str]] = None,
-        test_targets: Optional[list[str]] = None,
-        test_workers: Optional[list[ModelWorker]] = None,
+        test_prefixes: list[str] | None = None,
+        logfile: str | None = None,
+        managers: dict[str, Any] | None = None,
+        test_goals: list[str] | None = None,
+        test_targets: list[str] | None = None,
+        test_workers: list[ModelWorker] | None = None,
         **kwargs: Any,
     ) -> None:
         """
@@ -1549,7 +1549,7 @@ def __init__(
         self.tokenizer = tokenizer
         self.tasks: mp.JoinableQueue[Any] = mp.JoinableQueue()
         self.results: mp.JoinableQueue[Any] = mp.JoinableQueue()
-        self.process: Optional[mp.Process] = None
+        self.process: mp.Process | None = None
 
     @staticmethod
     def run(model: Any, tasks: mp.JoinableQueue[Any], results: mp.JoinableQueue[Any]) -> None:
diff --git a/pyrit/auxiliary_attacks/gcg/experiments/log.py b/pyrit/auxiliary_attacks/gcg/experiments/log.py
index bdd96c1ca4..68c7ded7eb 100644
--- a/pyrit/auxiliary_attacks/gcg/experiments/log.py
+++ b/pyrit/auxiliary_attacks/gcg/experiments/log.py
@@ -3,7 +3,7 @@
 
 import logging
 import subprocess as sp
-from typing import Any, Optional
+from typing import Any
 
 logger = logging.getLogger(__name__)
 
@@ -20,7 +20,7 @@
 def log_params(
     *,
     params: Any,
-    param_keys: Optional[list[str]] = None,
+    param_keys: list[str] | None = None,
 ) -> None:
     """
     Log selected parameters via Python logging.
diff --git a/pyrit/auxiliary_attacks/gcg/generator.py b/pyrit/auxiliary_attacks/gcg/generator.py
index cf353a2adf..4c812594e9 100644
--- a/pyrit/auxiliary_attacks/gcg/generator.py
+++ b/pyrit/auxiliary_attacks/gcg/generator.py
@@ -38,7 +38,7 @@
 import logging
 import time
 from dataclasses import dataclass, field
-from typing import Any, Optional, overload
+from typing import Any, overload
 
 import numpy as np
 import torch.multiprocessing as mp
@@ -93,8 +93,8 @@ class GCGContext(PromptGeneratorStrategyContext):
 
     workers: list[Any] = field(default_factory=list)
     test_workers: list[Any] = field(default_factory=list)
-    attack: Optional[Any] = None
-    logfile_path: Optional[str] = None
+    attack: Any | None = None
+    logfile_path: str | None = None
 
 
 class GCGResult(PromptGeneratorStrategyResult):
@@ -138,11 +138,11 @@ def __init__(
         self,
         *,
         models: list[GCGModelConfig],
-        algorithm: Optional[GCGAlgorithmConfig] = None,
-        strategy: Optional[GCGStrategyConfig] = None,
-        output: Optional[GCGOutputConfig] = None,
-        test_models: Optional[list[GCGModelConfig]] = None,
-        hf_token: Optional[str] = None,
+        algorithm: GCGAlgorithmConfig | None = None,
+        strategy: GCGStrategyConfig | None = None,
+        output: GCGOutputConfig | None = None,
+        test_models: list[GCGModelConfig] | None = None,
+        hf_token: str | None = None,
     ) -> None:
         """
         Initialize the GCG generator.
@@ -307,9 +307,9 @@ async def execute_async(
         *,
         goals: list[str],
         targets: list[str],
-        test_goals: Optional[list[str]] = None,
-        test_targets: Optional[list[str]] = None,
-        memory_labels: Optional[dict[str, str]] = None,
+        test_goals: list[str] | None = None,
+        test_targets: list[str] | None = None,
+        memory_labels: dict[str, str] | None = None,
         **kwargs: Any,
     ) -> GCGResult: ...
 
diff --git a/pyrit/backend/mappers/attack_mappers.py b/pyrit/backend/mappers/attack_mappers.py
index 5807c27bef..b93eceb64e 100644
--- a/pyrit/backend/mappers/attack_mappers.py
+++ b/pyrit/backend/mappers/attack_mappers.py
@@ -17,7 +17,7 @@
 import uuid
 from datetime import datetime, timedelta, timezone
 from pathlib import Path
-from typing import TYPE_CHECKING, Optional, cast
+from typing import TYPE_CHECKING, cast
 from urllib.parse import quote, urlparse
 
 from azure.identity.aio import DefaultAzureCredential
@@ -155,7 +155,7 @@ async def _sign_blob_url_async(*, blob_url: str) -> str:
         return blob_url
 
 
-def _resolve_media_url(*, value: Optional[str], data_type: str) -> Optional[str]:
+def _resolve_media_url(*, value: str | None, data_type: str) -> str | None:
     """
     For media path types, convert a local file path to a ``/api/media`` URL.
 
@@ -311,7 +311,7 @@ def pyrit_scores_to_dto(scores: list[PyritScore]) -> list[Score]:
     ]
 
 
-def _infer_mime_type(*, value: Optional[str], data_type: PromptDataType) -> Optional[str]:
+def _infer_mime_type(*, value: str | None, data_type: PromptDataType) -> str | None:
     """
     Infer MIME type from a value and its data type.
 
@@ -335,9 +335,9 @@ def _infer_mime_type(*, value: Optional[str], data_type: PromptDataType) -> Opti
 def _build_filename(
     *,
     data_type: str,
-    sha256: Optional[str],
-    value: Optional[str],
-) -> Optional[str]:
+    sha256: str | None,
+    value: str | None,
+) -> str | None:
     """
     Build a human-readable download filename from the data type and hash.
 
@@ -462,7 +462,7 @@ def request_piece_to_pyrit_message_piece(
     role: ChatMessageRole,
     conversation_id: str,
     sequence: int,
-    labels: Optional[dict[str, str]] = None,  # deprecated
+    labels: dict[str, str] | None = None,  # deprecated
 ) -> PyritMessagePiece:
     """
     Convert a single request piece DTO to a PyRIT MessagePiece domain object.
@@ -509,7 +509,7 @@ def request_to_pyrit_message(
     request: AddMessageRequest,
     conversation_id: str,
     sequence: int,
-    labels: Optional[dict[str, str]] = None,  # deprecated
+    labels: dict[str, str] | None = None,  # deprecated
 ) -> PyritMessage:
     """
     Build a PyRIT Message from an AddMessageRequest DTO.
diff --git a/pyrit/backend/mappers/converter_mappers.py b/pyrit/backend/mappers/converter_mappers.py
index f1d097762d..a71b5aa537 100644
--- a/pyrit/backend/mappers/converter_mappers.py
+++ b/pyrit/backend/mappers/converter_mappers.py
@@ -5,8 +5,6 @@
 Converter mappers – domain → DTO translation for converter-related models.
 """
 
-from typing import Optional
-
 from pyrit.backend.models.converters import ConverterInstance
 from pyrit.prompt_converter import PromptConverter
 
@@ -21,7 +19,7 @@ def converter_object_to_instance(
     converter_id: str,
     converter_obj: PromptConverter,
     *,
-    sub_converter_ids: Optional[list[str]] = None,
+    sub_converter_ids: list[str] | None = None,
 ) -> ConverterInstance:
     """
     Build a ConverterInstance DTO from a registry converter object.
diff --git a/pyrit/backend/middleware/auth.py b/pyrit/backend/middleware/auth.py
index db7de281ea..012af51912 100644
--- a/pyrit/backend/middleware/auth.py
+++ b/pyrit/backend/middleware/auth.py
@@ -18,7 +18,7 @@
 import logging
 import os
 from dataclasses import dataclass
-from typing import Any, Optional
+from typing import Any
 
 import httpx
 import jwt
@@ -241,7 +241,7 @@ async def _resolve_excess_groups_async(self, claims: dict[str, Any], token: str)
             logger.warning("Failed to resolve group memberships: %s", e)
             return []
 
-    def _validate_token(self, token: str) -> tuple[Optional[AuthenticatedUser], dict[str, Any]]:
+    def _validate_token(self, token: str) -> tuple[AuthenticatedUser | None, dict[str, Any]]:
         """
         Validate a JWT against Entra ID JWKS.
 
diff --git a/pyrit/backend/models/attacks.py b/pyrit/backend/models/attacks.py
index 2f98f78b7e..6cb739cb5e 100644
--- a/pyrit/backend/models/attacks.py
+++ b/pyrit/backend/models/attacks.py
@@ -9,7 +9,7 @@
 """
 
 from datetime import datetime
-from typing import Any, Literal, Optional
+from typing import Any, Literal
 
 from pydantic import BaseModel, Field
 
@@ -26,8 +26,8 @@ class Score(BaseModel):
     score_value: str = Field(
         ..., description="Score value ('true'/'false' for true_false, '0.0'-'1.0' for float_scale)"
     )
-    score_category: Optional[list[str]] = Field(None, description="Harm categories (e.g., ['hate', 'violence'])")
-    score_rationale: Optional[str] = Field(None, description="Explanation for the score")
+    score_category: list[str] | None = Field(None, description="Harm categories (e.g., ['hate', 'violence'])")
+    score_rationale: str | None = Field(None, description="Explanation for the score")
     scored_at: datetime = Field(..., description="When the score was generated")
 
 
@@ -46,24 +46,24 @@ class MessagePiece(BaseModel):
     converted_value_data_type: str = Field(
         default="text", description="Data type of the converted value: 'text', 'image', 'audio', etc."
     )
-    original_value: Optional[str] = Field(default=None, description="Original value before conversion")
-    original_value_mime_type: Optional[str] = Field(default=None, description="MIME type of original value")
+    original_value: str | None = Field(default=None, description="Original value before conversion")
+    original_value_mime_type: str | None = Field(default=None, description="MIME type of original value")
     converted_value: str = Field(..., description="Converted value (text or base64 for media)")
-    converted_value_mime_type: Optional[str] = Field(default=None, description="MIME type of converted value")
+    converted_value_mime_type: str | None = Field(default=None, description="MIME type of converted value")
     scores: list[Score] = Field(default_factory=list, description="Scores embedded in this piece")
     response_error: PromptResponseError = Field(
         default="none", description="Error status: none, processing, blocked, empty, unknown"
     )
-    response_error_description: Optional[str] = Field(
+    response_error_description: str | None = Field(
         default=None, description="Description of the error if response_error is not 'none'"
     )
-    original_filename: Optional[str] = Field(
+    original_filename: str | None = Field(
         default=None, description="Original filename extracted from file path or blob URL"
     )
-    converted_filename: Optional[str] = Field(
+    converted_filename: str | None = Field(
         default=None, description="Converted filename extracted from file path or blob URL"
     )
-    prompt_metadata: Optional[dict[str, Any]] = Field(
+    prompt_metadata: dict[str, Any] | None = Field(
         default=None, description="Metadata associated with the piece (e.g., video_id for remix mode)"
     )
 
@@ -86,8 +86,8 @@ class TargetInfo(BaseModel):
     """Target information extracted from the stored TargetIdentifier."""
 
     target_type: str = Field(..., description="Target class name (e.g., 'OpenAIChatTarget')")
-    endpoint: Optional[str] = Field(None, description="Target endpoint URL")
-    model_name: Optional[str] = Field(None, description="Model or deployment name")
+    endpoint: str | None = Field(None, description="Target endpoint URL")
+    model_name: str | None = Field(None, description="Model or deployment name")
 
 
 class RetryEventResponse(BaseModel):
@@ -110,20 +110,18 @@ class AttackSummary(BaseModel):
     attack_result_id: str = Field(..., description="Database-assigned unique ID for this AttackResult")
     conversation_id: str = Field(..., description="Primary conversation of this attack result")
     attack_type: str = Field("", description="Attack class name (e.g., 'CrescendoAttack', 'ManualAttack')")
-    attack_specific_params: Optional[dict[str, Any]] = Field(None, description="Additional attack-specific parameters")
-    target: Optional[TargetInfo] = Field(None, description="Target information from the stored identifier")
+    attack_specific_params: dict[str, Any] | None = Field(None, description="Additional attack-specific parameters")
+    target: TargetInfo | None = Field(None, description="Target information from the stored identifier")
     converters: list[str] = Field(
         default_factory=list, description="Request converter class names applied in this attack"
     )
     objective: str = Field("", description="Natural-language description of the attacker's objective")
-    outcome: Optional[Literal["undetermined", "success", "failure", "error"]] = Field(
+    outcome: Literal["undetermined", "success", "failure", "error"] | None = Field(
         None, description="Attack outcome (null if not yet determined)"
     )
     outcome_reason: str | None = Field(None, description="Reason for the outcome")
     last_response: str | None = Field(None, description="Model response from the final turn")
-    last_message_preview: Optional[str] = Field(
-        None, description="Preview of the last message (truncated to ~100 chars)"
-    )
+    last_message_preview: str | None = Field(None, description="Preview of the last message (truncated to ~100 chars)")
     score_value: str | None = Field(None, description="Score value from the objective scorer")
     executed_turns: int = Field(0, ge=0, description="Number of turns executed")
     execution_time_ms: int = Field(0, ge=0, description="Execution time in milliseconds")
@@ -195,13 +193,13 @@ class MessagePieceRequest(BaseModel):
 
     data_type: str = Field(default="text", description="Data type: 'text', 'image', 'audio', etc.")
     original_value: str = Field(..., description="Original value (text or base64 for media)")
-    converted_value: Optional[str] = Field(None, description="Converted value. If provided, bypasses converters.")
-    mime_type: Optional[str] = Field(None, description="MIME type for media content")
-    prompt_metadata: Optional[dict[str, Any]] = Field(
+    converted_value: str | None = Field(None, description="Converted value. If provided, bypasses converters.")
+    mime_type: str | None = Field(None, description="MIME type for media content")
+    prompt_metadata: dict[str, Any] | None = Field(
         None,
         description="Metadata to attach to the piece (e.g., {'video_id': '...'} for remix mode).",
     )
-    original_prompt_id: Optional[str] = Field(
+    original_prompt_id: str | None = Field(
         None,
         description="ID of the source piece when prepending from an existing conversation. "
         "Preserves lineage so the new piece traces back to the original.",
@@ -231,18 +229,16 @@ class CreateAttackRequest(BaseModel):
     supplied in ``labels`` (typically the current operator's labels).
     """
 
-    name: Optional[str] = Field(None, description="Attack name/label")
+    name: str | None = Field(None, description="Attack name/label")
     target_registry_name: str = Field(..., description="Target registry name to attack")
-    source_conversation_id: Optional[str] = Field(
+    source_conversation_id: str | None = Field(
         None, description="Conversation to branch from (clone messages into the new attack)"
     )
-    cutoff_index: Optional[int] = Field(
-        None, description="Include messages up to and including this turn index (0-based)"
-    )
-    prepended_conversation: Optional[list[PrependedMessageRequest]] = Field(
+    cutoff_index: int | None = Field(None, description="Include messages up to and including this turn index (0-based)")
+    prepended_conversation: list[PrependedMessageRequest] | None = Field(
         None, description="Messages to prepend (system prompts, branching context)", max_length=200
     )
-    labels: Optional[dict[str, str]] = Field(None, description="User-defined labels for filtering")
+    labels: dict[str, str] | None = Field(None, description="User-defined labels for filtering")
 
 
 class CreateAttackResponse(BaseModel):
@@ -274,8 +270,8 @@ class ConversationSummary(BaseModel):
 
     conversation_id: str = Field(..., description="Unique conversation identifier")
     message_count: int = Field(0, description="Number of messages in this conversation")
-    last_message_preview: Optional[str] = Field(None, description="Preview of the last message")
-    created_at: Optional[datetime] = Field(None, description="Timestamp of the first message")
+    last_message_preview: str | None = Field(None, description="Preview of the last message")
+    created_at: datetime | None = Field(None, description="Timestamp of the first message")
 
 
 class AttackConversationsResponse(BaseModel):
@@ -297,10 +293,8 @@ class CreateConversationRequest(BaseModel):
     the cutoff turn, preserving tracking relationships (original_prompt_id).
     """
 
-    source_conversation_id: Optional[str] = Field(None, description="Conversation to branch from")
-    cutoff_index: Optional[int] = Field(
-        None, description="Include messages up to and including this turn index (0-based)"
-    )
+    source_conversation_id: str | None = Field(None, description="Conversation to branch from")
+    cutoff_index: int | None = Field(None, description="Include messages up to and including this turn index (0-based)")
 
 
 class CreateConversationResponse(BaseModel):
@@ -344,11 +338,11 @@ class AddMessageRequest(BaseModel):
         default=True,
         description="If True, send to target and wait for response. If False, just store in memory.",
     )
-    target_registry_name: Optional[str] = Field(
+    target_registry_name: str | None = Field(
         None,
         description="Target registry name. Required when send=True so the backend knows which target to use.",
     )
-    converter_ids: Optional[list[str]] = Field(
+    converter_ids: list[str] | None = Field(
         None, description="Converter instance IDs to apply (overrides attack-level)"
     )
     target_conversation_id: str = Field(
@@ -356,7 +350,7 @@ class AddMessageRequest(BaseModel):
         description="The conversation_id to store and send messages under. "
         "Usually the attack's main conversation, but can be a related conversation.",
     )
-    labels: Optional[dict[str, str]] = Field(
+    labels: dict[str, str] | None = Field(
         None,
         description="Labels to attach to every message piece. "
         "Falls back to labels from existing pieces in the conversation.",
diff --git a/pyrit/backend/models/common.py b/pyrit/backend/models/common.py
index 0a2e00e6b5..36767467cc 100644
--- a/pyrit/backend/models/common.py
+++ b/pyrit/backend/models/common.py
@@ -7,7 +7,7 @@
 Includes pagination, error handling (RFC 7807), and shared base models.
 """
 
-from typing import Any, Optional
+from typing import Any
 
 from pydantic import BaseModel, Field
 
@@ -17,8 +17,8 @@ class PaginationInfo(BaseModel):
 
     limit: int = Field(..., description="Maximum items per page")
     has_more: bool = Field(..., description="Whether more items exist")
-    next_cursor: Optional[str] = Field(None, description="Cursor for next page")
-    prev_cursor: Optional[str] = Field(None, description="Cursor for previous page")
+    next_cursor: str | None = Field(None, description="Cursor for next page")
+    prev_cursor: str | None = Field(None, description="Cursor for previous page")
 
 
 class FieldError(BaseModel):
@@ -26,8 +26,8 @@ class FieldError(BaseModel):
 
     field: str = Field(..., description="Field name with path (e.g., 'pieces[0].data_type')")
     message: str = Field(..., description="Error message")
-    code: Optional[str] = Field(None, description="Error code")
-    value: Optional[Any] = Field(None, description="The invalid value")
+    code: str | None = Field(None, description="Error code")
+    value: Any | None = Field(None, description="The invalid value")
 
 
 class ProblemDetail(BaseModel):
@@ -41,8 +41,8 @@ class ProblemDetail(BaseModel):
     title: str = Field(..., description="Short human-readable summary")
     status: int = Field(..., description="HTTP status code")
     detail: str = Field(..., description="Human-readable explanation")
-    instance: Optional[str] = Field(None, description="URI of the specific occurrence")
-    errors: Optional[list[FieldError]] = Field(None, description="Field-level errors for validation")
+    instance: str | None = Field(None, description="URI of the specific occurrence")
+    errors: list[FieldError] | None = Field(None, description="Field-level errors for validation")
 
 
 # Sensitive field patterns to filter from identifiers
diff --git a/pyrit/backend/models/converters.py b/pyrit/backend/models/converters.py
index ba5ca5390d..dd216b84b3 100644
--- a/pyrit/backend/models/converters.py
+++ b/pyrit/backend/models/converters.py
@@ -7,7 +7,7 @@
 This module defines the Instance models and preview functionality.
 """
 
-from typing import Any, Optional
+from typing import Any
 
 from pydantic import BaseModel, Field
 
@@ -38,9 +38,9 @@ class ConverterParameterSchema(BaseModel):
     name: str = Field(..., description="Parameter name")
     type_name: str = Field(..., description="Human-readable type (e.g. 'str', 'int', 'Literal[...]')")
     required: bool = Field(..., description="Whether the parameter must be provided")
-    default_value: Optional[str] = Field(None, description="String representation of default value, if any")
-    choices: Optional[list[str]] = Field(None, description="Allowed values for Literal types")
-    description: Optional[str] = Field(None, description="Parameter description from docstring")
+    default_value: str | None = Field(None, description="String representation of default value, if any")
+    choices: list[str] | None = Field(None, description="Allowed values for Literal types")
+    description: str | None = Field(None, description="Parameter description from docstring")
 
 
 class ConverterCatalogEntry(BaseModel):
@@ -57,7 +57,7 @@ class ConverterCatalogEntry(BaseModel):
         default_factory=list, description="Constructor parameters for dynamic form generation"
     )
     is_llm_based: bool = Field(False, description="Whether this converter requires an LLM target")
-    description: Optional[str] = Field(None, description="Short description of the converter from its docstring")
+    description: str | None = Field(None, description="Short description of the converter from its docstring")
 
 
 class ConverterCatalogResponse(BaseModel):
@@ -76,17 +76,17 @@ class ConverterInstance(BaseModel):
 
     converter_id: str = Field(..., description="Unique converter instance identifier")
     converter_type: str = Field(..., description="Converter class name (e.g., 'Base64Converter')")
-    display_name: Optional[str] = Field(None, description="Human-readable display name")
+    display_name: str | None = Field(None, description="Human-readable display name")
     supported_input_types: list[str] = Field(
         default_factory=list, description="Input data types supported by this converter"
     )
     supported_output_types: list[str] = Field(
         default_factory=list, description="Output data types produced by this converter"
     )
-    converter_specific_params: Optional[dict[str, Any]] = Field(
+    converter_specific_params: dict[str, Any] | None = Field(
         None, description="Additional converter-specific parameters"
     )
-    sub_converter_ids: Optional[list[str]] = Field(
+    sub_converter_ids: list[str] | None = Field(
         None, description="Converter IDs of sub-converters (for pipelines/composites)"
     )
 
@@ -101,7 +101,7 @@ class CreateConverterRequest(BaseModel):
     """Request to create a new converter instance."""
 
     type: str = Field(..., description="Converter type (e.g., 'Base64Converter')")
-    display_name: Optional[str] = Field(None, description="Human-readable display name")
+    display_name: str | None = Field(None, description="Human-readable display name")
     params: dict[str, Any] = Field(
         default_factory=dict,
         description="Converter constructor parameters",
@@ -113,7 +113,7 @@ class CreateConverterResponse(BaseModel):
 
     converter_id: str = Field(..., description="Unique converter instance identifier")
     converter_type: str = Field(..., description="Converter class name")
-    display_name: Optional[str] = Field(None, description="Human-readable display name")
+    display_name: str | None = Field(None, description="Human-readable display name")
 
 
 # ============================================================================
diff --git a/pyrit/backend/models/scenarios.py b/pyrit/backend/models/scenarios.py
index 54480b76c7..aaac688cf0 100644
--- a/pyrit/backend/models/scenarios.py
+++ b/pyrit/backend/models/scenarios.py
@@ -10,7 +10,7 @@
 
 from datetime import datetime
 from enum import Enum
-from typing import Any, Optional
+from typing import Any
 
 from pydantic import BaseModel, Field
 
@@ -40,7 +40,7 @@ class RegisteredScenario(BaseModel):
     )
     all_strategies: list[str] = Field(..., description="All available concrete strategy names")
     default_datasets: list[str] = Field(..., description="Default dataset names used by the scenario")
-    max_dataset_size: Optional[int] = Field(None, description="Maximum items per dataset (None means unlimited)")
+    max_dataset_size: int | None = Field(None, description="Maximum items per dataset (None means unlimited)")
     supported_parameters: list[ScenarioParameterSummary] = Field(
         default_factory=list, description="Scenario-declared custom parameters"
     )
diff --git a/pyrit/backend/models/targets.py b/pyrit/backend/models/targets.py
index da512da155..944fbc358f 100644
--- a/pyrit/backend/models/targets.py
+++ b/pyrit/backend/models/targets.py
@@ -11,7 +11,7 @@
 This module defines the Instance models for runtime target management.
 """
 
-from typing import Any, Literal, Optional
+from typing import Any, Literal
 
 from pydantic import BaseModel, Field
 
@@ -56,16 +56,14 @@ class TargetInstance(BaseModel):
 
     target_registry_name: str = Field(..., description="Target registry key (e.g., 'azure_openai_chat')")
     target_type: str = Field(..., description="Target class name (e.g., 'OpenAIChatTarget')")
-    endpoint: Optional[str] = Field(None, description="Target endpoint URL")
-    model_name: Optional[str] = Field(None, description="Model or deployment name used in API calls")
-    underlying_model_name: Optional[str] = Field(
-        None, description="Underlying model name if different (e.g., 'gpt-4o')"
-    )
-    temperature: Optional[float] = Field(None, description="Temperature parameter for generation")
-    top_p: Optional[float] = Field(None, description="Top-p parameter for generation")
-    max_requests_per_minute: Optional[int] = Field(None, description="Maximum requests per minute")
+    endpoint: str | None = Field(None, description="Target endpoint URL")
+    model_name: str | None = Field(None, description="Model or deployment name used in API calls")
+    underlying_model_name: str | None = Field(None, description="Underlying model name if different (e.g., 'gpt-4o')")
+    temperature: float | None = Field(None, description="Temperature parameter for generation")
+    top_p: float | None = Field(None, description="Top-p parameter for generation")
+    max_requests_per_minute: int | None = Field(None, description="Maximum requests per minute")
     capabilities: TargetCapabilitiesInfo = Field(..., description="Structured snapshot of target capabilities")
-    target_specific_params: Optional[dict[str, Any]] = Field(None, description="Additional target-specific parameters")
+    target_specific_params: dict[str, Any] | None = Field(None, description="Additional target-specific parameters")
 
 
 class TargetListResponse(BaseModel):
diff --git a/pyrit/backend/pyrit_backend.py b/pyrit/backend/pyrit_backend.py
index 0770ae501a..6c792f383d 100644
--- a/pyrit/backend/pyrit_backend.py
+++ b/pyrit/backend/pyrit_backend.py
@@ -17,12 +17,11 @@
 import sys
 from argparse import ArgumentParser, Namespace, RawDescriptionHelpFormatter
 from pathlib import Path
-from typing import Optional
 
 from pyrit.common.cli_helpers import CONFIG_FILE_HELP, validate_log_level_argparse
 
 
-def parse_args(*, args: Optional[list[str]] = None) -> Namespace:
+def parse_args(*, args: list[str] | None = None) -> Namespace:
     """
     Parse command-line arguments for the PyRIT backend server.
 
@@ -88,7 +87,7 @@ def parse_args(*, args: Optional[list[str]] = None) -> Namespace:
     return parser.parse_args(args)
 
 
-def main(*, args: Optional[list[str]] = None) -> int:
+def main(*, args: list[str] | None = None) -> int:
     """
     Start the PyRIT backend server.
 
diff --git a/pyrit/backend/routes/attacks.py b/pyrit/backend/routes/attacks.py
index d6844d5041..7f41ec4339 100644
--- a/pyrit/backend/routes/attacks.py
+++ b/pyrit/backend/routes/attacks.py
@@ -10,7 +10,7 @@
 
 import logging
 from collections.abc import Sequence
-from typing import Literal, Optional
+from typing import Literal
 
 from fastapi import APIRouter, HTTPException, Query, status
 
@@ -39,7 +39,7 @@
 router = APIRouter(prefix="/attacks", tags=["attacks"])
 
 
-def _parse_labels(label_params: Optional[list[str]]) -> Optional[dict[str, str | Sequence[str]]]:
+def _parse_labels(label_params: list[str] | None) -> dict[str, str | Sequence[str]] | None:
     """
     Parse 'key:value' label query params into a dict grouping values by key.
 
@@ -69,13 +69,13 @@ def _parse_labels(label_params: Optional[list[str]]) -> Optional[dict[str, str |
     response_model=AttackListResponse,
 )
 async def list_attacks(  # pyrit-async-suffix-exempt
-    attack_types: Optional[list[str]] = Query(
+    attack_types: list[str] | None = Query(
         None,
         description="Filter by attack type names. May be specified multiple times to OR-match "
         "across types (e.g. ?attack_types=A&attack_types=B). Case-insensitive. "
         "Omit to return all attacks regardless of type.",
     ),
-    converter_types: Optional[list[str]] = Query(
+    converter_types: list[str] | None = Query(
         None,
         description="Filter by converter type names. May be specified multiple times; "
         "combination semantics are controlled by converter_types_match "
@@ -88,24 +88,24 @@ async def list_attacks(  # pyrit-async-suffix-exempt
         description="How to combine multiple converter_types: 'any' (attack has at least one) "
         "or 'all' (attack has every one). Defaults to 'all'.",
     ),
-    has_converters: Optional[bool] = Query(
+    has_converters: bool | None = Query(
         None,
         description="Filter by converter presence. true = attacks with at least one converter; "
         "false = attacks with no converters. Omit for no filter.",
     ),
-    outcome: Optional[Literal["undetermined", "success", "failure", "error"]] = Query(
+    outcome: Literal["undetermined", "success", "failure", "error"] | None = Query(
         None, description="Filter by outcome"
     ),
-    label: Optional[list[str]] = Query(
+    label: list[str] | None = Query(
         None,
         description="Filter by labels (format: key:value). May be specified multiple times; "
         "OR-matched within a key, AND-matched across keys "
         "(e.g. ?label=op:red&label=op:blue matches op=red OR op=blue).",
     ),
-    min_turns: Optional[int] = Query(None, ge=0, description="Filter by minimum executed turns"),
-    max_turns: Optional[int] = Query(None, ge=0, description="Filter by maximum executed turns"),
+    min_turns: int | None = Query(None, ge=0, description="Filter by minimum executed turns"),
+    max_turns: int | None = Query(None, ge=0, description="Filter by maximum executed turns"),
     limit: int = Query(20, ge=1, le=100, description="Maximum items per page"),
-    cursor: Optional[str] = Query(
+    cursor: str | None = Query(
         None,
         description="Pagination cursor: the attack_result_id of the last item from the previous page. "
         "Omit to start from the beginning. The response includes next_cursor for the next page.",
diff --git a/pyrit/backend/routes/scenarios.py b/pyrit/backend/routes/scenarios.py
index d75857210b..941d8021fb 100644
--- a/pyrit/backend/routes/scenarios.py
+++ b/pyrit/backend/routes/scenarios.py
@@ -12,8 +12,6 @@
     /api/scenarios/runs          — scenario execution lifecycle
 """
 
-from typing import Optional
-
 from fastapi import APIRouter, HTTPException, Query, status
 
 from pyrit.backend.models.common import ProblemDetail
@@ -41,7 +39,7 @@
 )
 async def list_scenarios(  # pyrit-async-suffix-exempt
     limit: int = Query(50, ge=1, le=200, description="Maximum items per page"),
-    cursor: Optional[str] = Query(None, description="Pagination cursor (scenario_name to start after)"),
+    cursor: str | None = Query(None, description="Pagination cursor (scenario_name to start after)"),
 ) -> ListRegisteredScenariosResponse:
     """
     List all available scenarios.
diff --git a/pyrit/backend/routes/targets.py b/pyrit/backend/routes/targets.py
index 5a05ea41fd..bea53ddef2 100644
--- a/pyrit/backend/routes/targets.py
+++ b/pyrit/backend/routes/targets.py
@@ -8,8 +8,6 @@
 Target types are set at app startup via initializers - you cannot add new types at runtime.
 """
 
-from typing import Optional
-
 from fastapi import APIRouter, HTTPException, Query, status
 
 from pyrit.backend.models.common import ProblemDetail
@@ -32,7 +30,7 @@
 )
 async def list_targets(  # pyrit-async-suffix-exempt
     limit: int = Query(50, ge=1, le=200, description="Maximum items per page"),
-    cursor: Optional[str] = Query(None, description="Pagination cursor (target_registry_name)"),
+    cursor: str | None = Query(None, description="Pagination cursor (target_registry_name)"),
 ) -> TargetListResponse:
     """
     List target instances with pagination.
diff --git a/pyrit/backend/routes/version.py b/pyrit/backend/routes/version.py
index b59d176158..2d75c200aa 100644
--- a/pyrit/backend/routes/version.py
+++ b/pyrit/backend/routes/version.py
@@ -6,7 +6,6 @@
 import json
 import logging
 from pathlib import Path
-from typing import Optional
 
 from fastapi import APIRouter, Request
 from pydantic import BaseModel
@@ -23,12 +22,12 @@ class VersionResponse(BaseModel):
     """Version information response model."""
 
     version: str
-    source: Optional[str] = None
-    commit: Optional[str] = None
-    modified: Optional[bool] = None
+    source: str | None = None
+    commit: str | None = None
+    modified: bool | None = None
     display: str
-    database_info: Optional[str] = None
-    default_labels: Optional[dict[str, str]] = None
+    database_info: str | None = None
+    default_labels: dict[str, str] | None = None
 
 
 @router.get("", response_model=VersionResponse)
@@ -62,7 +61,7 @@ async def get_version_async(request: Request) -> VersionResponse:
             logger.warning(f"Failed to load build info: {e}")
 
     # Detect current database backend
-    database_info: Optional[str] = None
+    database_info: str | None = None
     try:
         memory = CentralMemory.get_memory_instance()
         db_type = type(memory).__name__
@@ -74,7 +73,7 @@ async def get_version_async(request: Request) -> VersionResponse:
         logger.debug(f"Could not detect database info: {e}")
 
     # Read default labels from app state (set by pyrit_backend CLI)
-    default_labels: Optional[dict[str, str]] = getattr(request.app.state, "default_labels", None) or None
+    default_labels: dict[str, str] | None = getattr(request.app.state, "default_labels", None) or None
 
     return VersionResponse(
         version=version,
diff --git a/pyrit/cli/_banner.py b/pyrit/cli/_banner.py
index 0c8d4719eb..21e1f1c5bd 100644
--- a/pyrit/cli/_banner.py
+++ b/pyrit/cli/_banner.py
@@ -21,7 +21,6 @@
 import time
 from dataclasses import dataclass, field
 from enum import Enum
-from typing import Optional
 
 from pyrit.cli._banner_assets import BRAILLE_RACCOON, PYRIT_LETTERS, PYRIT_WIDTH, RACCOON_TAIL
 
@@ -199,7 +198,7 @@ def _build_static_banner() -> StaticBannerData:
     color_map: dict[int, ColorRole] = {}
     segment_colors: dict[int, list[tuple[int, int, ColorRole]]] = {}
 
-    def add(line: str, role: ColorRole, segments: Optional[list[tuple[int, int, ColorRole]]] = None) -> None:
+    def add(line: str, role: ColorRole, segments: list[tuple[int, int, ColorRole]] | None = None) -> None:
         idx = len(lines)
         color_map[idx] = role
         if segments:
@@ -559,14 +558,14 @@ def _render_line_with_segments(
     """
     reset = _get_color(ColorRole.RESET, theme)
     # Build per-character color map (later segments override earlier ones)
-    char_roles: list[Optional[ColorRole]] = [None] * len(line)
+    char_roles: list[ColorRole | None] = [None] * len(line)
     for start, end, role in segments:
         for pos in range(start, min(end, len(line))):
             char_roles[pos] = role
 
     # Group consecutive same-role characters for efficient rendering
     result: list[str] = []
-    current_role: Optional[ColorRole] = None
+    current_role: ColorRole | None = None
     for pos, ch in enumerate(line):
         char_role = char_roles[pos]
         if char_role != current_role:
diff --git a/pyrit/cli/_cli_args.py b/pyrit/cli/_cli_args.py
index e982b6ae06..a53ac152ef 100644
--- a/pyrit/cli/_cli_args.py
+++ b/pyrit/cli/_cli_args.py
@@ -21,7 +21,7 @@
 import logging
 import shlex
 from pathlib import Path
-from typing import TYPE_CHECKING, Any, Optional, get_origin
+from typing import TYPE_CHECKING, Any, get_origin
 
 from pyrit.common.cli_helpers import (
     CONFIG_FILE_HELP,
@@ -67,7 +67,7 @@ def validate_database(*, database: str) -> str:
     return database
 
 
-def validate_integer(value: str, *, name: str = "value", min_value: Optional[int] = None) -> int:
+def validate_integer(value: str, *, name: str = "value", min_value: int | None = None) -> int:
     """
     Validate and parse an integer value.
 
@@ -492,7 +492,7 @@ def _parse_shell_arguments(*, parts: list[str], arg_specs: list[_ArgSpec]) -> di
     return result
 
 
-def parse_run_arguments(*, args_string: str, declared_params: Optional[list[Parameter]] = None) -> dict[str, Any]:
+def parse_run_arguments(*, args_string: str, declared_params: list[Parameter] | None = None) -> dict[str, Any]:
     """
     Parse run command arguments from a string (for shell mode).
 
@@ -643,7 +643,7 @@ def extract_scenario_args(*, parsed: dict[str, Any]) -> dict[str, Any]:
 # ---------------------------------------------------------------------------
 
 
-def build_parameters_from_api(*, api_params: list[dict[str, Any]]) -> Optional[list[Parameter]]:
+def build_parameters_from_api(*, api_params: list[dict[str, Any]]) -> list[Parameter] | None:
     """
     Build ``Parameter`` objects from a scenario catalog's ``supported_parameters``.
 
@@ -669,7 +669,7 @@ def build_parameters_from_api(*, api_params: list[dict[str, Any]]) -> Optional[l
         else:
             resolved_type = type_map.get(type_display)
         raw_choices = p.get("choices")
-        choices: Optional[tuple[Any, ...]] = tuple(raw_choices) if raw_choices else None
+        choices: tuple[Any, ...] | None = tuple(raw_choices) if raw_choices else None
         parameters.append(
             Parameter(
                 name=p["name"],
@@ -699,7 +699,7 @@ def add_common_arguments(parser: argparse.ArgumentParser) -> None:
 
 def merge_config_scenario_args(
     *,
-    config_scenario: Optional[ScenarioConfig],
+    config_scenario: ScenarioConfig | None,
     effective_scenario_name: str,
     cli_args: dict[str, Any],
 ) -> dict[str, Any]:
diff --git a/pyrit/cli/pyrit_scan.py b/pyrit/cli/pyrit_scan.py
index 57ee0a3326..1e4467f929 100644
--- a/pyrit/cli/pyrit_scan.py
+++ b/pyrit/cli/pyrit_scan.py
@@ -17,7 +17,7 @@
 import sys
 from argparse import ArgumentParser, Namespace, RawDescriptionHelpFormatter
 from pathlib import Path
-from typing import Any, Optional
+from typing import Any
 
 from pyrit.cli._cli_args import (
     ARG_HELP,
@@ -332,7 +332,7 @@ def _extract_scenario_args(*, parsed: Namespace) -> dict[str, Any]:
     }
 
 
-def parse_args(args: Optional[list[str]] = None) -> Namespace:
+def parse_args(args: list[str] | None = None) -> Namespace:
     """
     Parse command-line arguments (pass 1 — tolerant of scenario-declared flags).
 
@@ -760,7 +760,7 @@ async def _run_async(*, parsed_args: Namespace) -> int:
         return 1
 
 
-def main(args: Optional[list[str]] = None) -> int:
+def main(args: list[str] | None = None) -> int:
     """
     Start the PyRIT scanner CLI.
 
diff --git a/pyrit/cli/pyrit_shell.py b/pyrit/cli/pyrit_shell.py
index 78dbed1aeb..1a0760eb7c 100644
--- a/pyrit/cli/pyrit_shell.py
+++ b/pyrit/cli/pyrit_shell.py
@@ -18,7 +18,7 @@
 import sys
 import threading
 from pathlib import Path
-from typing import TYPE_CHECKING, Any, Optional, TypeVar
+from typing import TYPE_CHECKING, Any, TypeVar
 
 from pyrit.cli import _banner as banner
 
@@ -173,7 +173,7 @@ def _ensure_client(self) -> bool:
         self._start_server = False  # only auto-start once
         return True
 
-    def cmdloop(self, intro: Optional[str] = None) -> None:
+    def cmdloop(self, intro: str | None = None) -> None:
         """Override cmdloop to play animated banner before starting the REPL."""
         if intro is None:
             prev_disable = logging.root.manager.disable
diff --git a/pyrit/common/default_values.py b/pyrit/common/default_values.py
index 9dbcba427f..4334cfb5d2 100644
--- a/pyrit/common/default_values.py
+++ b/pyrit/common/default_values.py
@@ -3,7 +3,7 @@
 
 import logging
 import os
-from typing import Any, Optional
+from typing import Any
 
 logger = logging.getLogger(__name__)
 
@@ -38,7 +38,7 @@ def get_required_value(*, env_var_name: str, passed_value: Any) -> Any:
     raise ValueError(f"Environment variable {env_var_name} is required")
 
 
-def get_non_required_value(*, env_var_name: str, passed_value: Optional[str] = None) -> str:
+def get_non_required_value(*, env_var_name: str, passed_value: str | None = None) -> str:
     """
     Get a non-required value from an environment variable or a passed value,
     preferring the passed value.
diff --git a/pyrit/common/net_utility.py b/pyrit/common/net_utility.py
index eb75f5616e..17d944e1e2 100644
--- a/pyrit/common/net_utility.py
+++ b/pyrit/common/net_utility.py
@@ -1,7 +1,7 @@
 # Copyright (c) Microsoft Corporation.
 # Licensed under the MIT license.
 
-from typing import Any, Literal, Optional, cast, overload
+from typing import Any, Literal, cast, overload
 from urllib.parse import parse_qs, urlparse, urlunparse
 
 import httpx
@@ -88,10 +88,10 @@ async def make_request_and_raise_if_error_async(
     method: str,
     post_type: PostType = "json",
     debug: bool = False,
-    extra_url_parameters: Optional[dict[str, str]] = None,
-    request_body: Optional[dict[str, object]] = None,
-    files: Optional[dict[str, tuple[str, bytes, str]]] = None,
-    headers: Optional[dict[str, str]] = None,
+    extra_url_parameters: dict[str, str] | None = None,
+    request_body: dict[str, object] | None = None,
+    files: dict[str, tuple[str, bytes, str]] | None = None,
+    headers: dict[str, str] | None = None,
     **httpx_client_kwargs: Any,
 ) -> httpx.Response:
     """
diff --git a/pyrit/common/utils.py b/pyrit/common/utils.py
index a7203ca336..d4a75e579c 100644
--- a/pyrit/common/utils.py
+++ b/pyrit/common/utils.py
@@ -8,12 +8,12 @@
 import math
 import random
 from pathlib import Path
-from typing import Any, Optional, TypeVar, Union
+from typing import Any, TypeVar
 
 logger = logging.getLogger(__name__)
 
 
-def verify_and_resolve_path(path: Union[str, Path]) -> Path:
+def verify_and_resolve_path(path: str | Path) -> Path:
     """
     Verify that a path is valid and resolve it to an absolute path.
 
@@ -39,9 +39,7 @@ def verify_and_resolve_path(path: Union[str, Path]) -> Path:
     return path_obj
 
 
-def combine_dict(
-    existing_dict: Optional[dict[str, Any]] = None, new_dict: Optional[dict[str, Any]] = None
-) -> dict[str, Any]:
+def combine_dict(existing_dict: dict[str, Any] | None = None, new_dict: dict[str, Any] | None = None) -> dict[str, Any]:
     """
     Combine two dictionaries containing string keys and values into one.
 
@@ -58,7 +56,7 @@ def combine_dict(
     return result
 
 
-def combine_list(list1: Union[str, list[str]], list2: Union[str, list[str]]) -> list[str]:
+def combine_list(list1: str | list[str], list2: str | list[str]) -> list[str]:
     """
     Combine two lists or strings into a single list with unique values.
 
@@ -126,7 +124,7 @@ def to_sha256(data: str) -> str:
 
 
 def warn_if_set(
-    *, config: Any, unused_fields: list[str], log: Union[logging.Logger, logging.LoggerAdapter[logging.Logger]] = logger
+    *, config: Any, unused_fields: list[str], log: logging.Logger | logging.LoggerAdapter[logging.Logger] = logger
 ) -> None:
     """
     Warn about unused parameters in configurations.
@@ -169,8 +167,8 @@ def get_kwarg_param(
     param_name: str,
     expected_type: type[_T],
     required: bool = True,
-    default_value: Optional[_T] = None,
-) -> Optional[_T]:
+    default_value: _T | None = None,
+) -> _T | None:
     """
     Validate and extract a parameter from kwargs.
 
diff --git a/pyrit/common/yaml_loadable.py b/pyrit/common/yaml_loadable.py
index a7857b7ad7..2fb4422c73 100644
--- a/pyrit/common/yaml_loadable.py
+++ b/pyrit/common/yaml_loadable.py
@@ -3,7 +3,7 @@
 
 import abc
 from pathlib import Path
-from typing import TypeVar, Union
+from typing import TypeVar
 
 import yaml
 
@@ -18,7 +18,7 @@ class YamlLoadable(abc.ABC):  # noqa: B024
     """
 
     @classmethod
-    def from_yaml_file(cls: type[T], file: Union[Path | str]) -> T:
+    def from_yaml_file(cls: type[T], file: Path | str) -> T:
         """
         Create a new object from a YAML file.
 
diff --git a/pyrit/datasets/executors/question_answer/wmdp_dataset.py b/pyrit/datasets/executors/question_answer/wmdp_dataset.py
index 1270c9b6c0..81f4711747 100644
--- a/pyrit/datasets/executors/question_answer/wmdp_dataset.py
+++ b/pyrit/datasets/executors/question_answer/wmdp_dataset.py
@@ -1,7 +1,6 @@
 # Copyright (c) Microsoft Corporation.
 # Licensed under the MIT license.
 
-from typing import Optional
 
 from datasets import load_dataset
 
@@ -12,7 +11,7 @@
 )
 
 
-def fetch_wmdp_dataset(category: Optional[str] = None) -> QuestionAnsweringDataset:
+def fetch_wmdp_dataset(category: str | None = None) -> QuestionAnsweringDataset:
     """
     Fetch WMDP examples and create a QuestionAnsweringDataset.
 
diff --git a/pyrit/datasets/jailbreak/text_jailbreak.py b/pyrit/datasets/jailbreak/text_jailbreak.py
index 6e5083bd42..380ee9c5c1 100644
--- a/pyrit/datasets/jailbreak/text_jailbreak.py
+++ b/pyrit/datasets/jailbreak/text_jailbreak.py
@@ -5,7 +5,7 @@
 import random
 import threading
 from pathlib import Path
-from typing import Any, Optional
+from typing import Any
 
 from pyrit.common.path import JAILBREAK_TEMPLATES_PATH
 from pyrit.models import SeedPrompt
@@ -18,7 +18,7 @@ class TextJailBreak:
     A class that manages jailbreak datasets (like DAN, etc.).
     """
 
-    _template_cache: Optional[dict[str, list[Path]]] = None
+    _template_cache: dict[str, list[Path]] | None = None
     _cache_lock: threading.Lock = threading.Lock()
 
     @classmethod
@@ -99,9 +99,9 @@ def _get_all_template_paths(cls) -> list[Path]:
     def __init__(
         self,
         *,
-        template_path: Optional[str] = None,
-        template_file_name: Optional[str] = None,
-        string_template: Optional[str] = None,
+        template_path: str | None = None,
+        template_file_name: str | None = None,
+        string_template: str | None = None,
         random_template: bool = False,
         **kwargs: Any,
     ) -> None:
@@ -208,7 +208,7 @@ def _apply_extra_kwargs(self, kwargs: dict[str, Any]) -> None:
             self.template.value = self.template.render_template_value_silent(**kwargs)
 
     @classmethod
-    def get_jailbreak_templates(cls, num_templates: Optional[int] = None) -> list[str]:
+    def get_jailbreak_templates(cls, num_templates: int | None = None) -> list[str]:
         """
         Retrieve all jailbreaks from the JAILBREAK_TEMPLATES_PATH.
 
diff --git a/pyrit/datasets/seed_datasets/local/local_dataset_loader.py b/pyrit/datasets/seed_datasets/local/local_dataset_loader.py
index 18f8343330..0ccae77fb1 100644
--- a/pyrit/datasets/seed_datasets/local/local_dataset_loader.py
+++ b/pyrit/datasets/seed_datasets/local/local_dataset_loader.py
@@ -5,7 +5,7 @@
 from collections.abc import Callable
 from dataclasses import fields
 from pathlib import Path
-from typing import Any, Optional
+from typing import Any
 
 import yaml
 
@@ -76,7 +76,7 @@ async def fetch_dataset_async(self, *, cache: bool = True) -> SeedDataset:
             logger.error(f"Failed to load local dataset from {self.file_path}: {e}")
             raise
 
-    async def _parse_metadata_async(self) -> Optional[SeedDatasetMetadata]:
+    async def _parse_metadata_async(self) -> SeedDatasetMetadata | None:
         """
         Extract metadata from a local YAML file and coerce raw values into typed schema fields.
 
diff --git a/pyrit/datasets/seed_datasets/remote/_image_cache.py b/pyrit/datasets/seed_datasets/remote/_image_cache.py
index dbc866a47b..bdb502ad23 100644
--- a/pyrit/datasets/seed_datasets/remote/_image_cache.py
+++ b/pyrit/datasets/seed_datasets/remote/_image_cache.py
@@ -14,7 +14,7 @@
 import logging
 from collections.abc import Mapping
 from pathlib import Path
-from typing import Any, Optional
+from typing import Any
 
 from pyrit.common.net_utility import make_request_and_raise_if_error_async
 from pyrit.models import data_serializer_factory
@@ -25,11 +25,11 @@
 async def fetch_and_cache_image_async(
     *,
     filename: str,
-    image_url: Optional[str] = None,
-    image_bytes: Optional[bytes] = None,
+    image_url: str | None = None,
+    image_bytes: bytes | None = None,
     log_prefix: str = "image-cache",
-    request_headers: Optional[Mapping[str, str]] = None,
-    request_timeout: Optional[float] = None,
+    request_headers: Mapping[str, str] | None = None,
+    request_timeout: float | None = None,
     follow_redirects: bool = False,
 ) -> str:
     """
diff --git a/pyrit/datasets/seed_datasets/remote/aegis_ai_content_safety_dataset.py b/pyrit/datasets/seed_datasets/remote/aegis_ai_content_safety_dataset.py
index 87e0d47b3c..1e38198fb6 100644
--- a/pyrit/datasets/seed_datasets/remote/aegis_ai_content_safety_dataset.py
+++ b/pyrit/datasets/seed_datasets/remote/aegis_ai_content_safety_dataset.py
@@ -2,7 +2,7 @@
 # Licensed under the MIT license.
 
 import logging
-from typing import Literal, Optional
+from typing import Literal
 
 from datasets import load_dataset
 
@@ -68,35 +68,34 @@ class _AegisContentSafetyDataset(_RemoteDatasetLoader):
     def __init__(
         self,
         *,
-        harm_categories: Optional[
-            list[
-                Literal[
-                    "Controlled/Regulated Substances",
-                    "Copyright/Trademark/Plagiarism",
-                    "Criminal Planning/Confessions",
-                    "Fraud/Deception",
-                    "Guns and Illegal Weapons",
-                    "Harassment",
-                    "Hate/Identity Hate",
-                    "High Risk Gov Decision Making",
-                    "Illegal Activity",
-                    "Immoral/Unethical",
-                    "Malware",
-                    "Manipulation",
-                    "Needs Caution",
-                    "Other",
-                    "PII/Privacy",
-                    "Political/Misinformation/Conspiracy",
-                    "Profanity",
-                    "Sexual",
-                    "Sexual (minor)",
-                    "Suicide and Self Harm",
-                    "Threat",
-                    "Unauthorized Advice",
-                    "Violence",
-                ]
+        harm_categories: list[
+            Literal[
+                "Controlled/Regulated Substances",
+                "Copyright/Trademark/Plagiarism",
+                "Criminal Planning/Confessions",
+                "Fraud/Deception",
+                "Guns and Illegal Weapons",
+                "Harassment",
+                "Hate/Identity Hate",
+                "High Risk Gov Decision Making",
+                "Illegal Activity",
+                "Immoral/Unethical",
+                "Malware",
+                "Manipulation",
+                "Needs Caution",
+                "Other",
+                "PII/Privacy",
+                "Political/Misinformation/Conspiracy",
+                "Profanity",
+                "Sexual",
+                "Sexual (minor)",
+                "Suicide and Self Harm",
+                "Threat",
+                "Unauthorized Advice",
+                "Violence",
             ]
-        ] = None,
+        ]
+        | None = None,
     ) -> None:
         """
         Initialize the NVIDIA Aegis AI Content Safety Dataset loader.
diff --git a/pyrit/datasets/seed_datasets/remote/agent_threat_rules_dataset.py b/pyrit/datasets/seed_datasets/remote/agent_threat_rules_dataset.py
index 338747b5e8..04839057da 100644
--- a/pyrit/datasets/seed_datasets/remote/agent_threat_rules_dataset.py
+++ b/pyrit/datasets/seed_datasets/remote/agent_threat_rules_dataset.py
@@ -3,7 +3,7 @@
 
 import logging
 from enum import Enum
-from typing import Literal, Optional
+from typing import Literal
 
 from pyrit.datasets.seed_datasets.remote.remote_dataset_loader import (
     _RemoteDatasetLoader,
@@ -134,10 +134,10 @@ def __init__(
             "db793f9/data/autoresearch/adversarial-samples.json"
         ),
         source_type: Literal["public_url", "file"] = "public_url",
-        categories: Optional[list[ATRCategory]] = None,
-        techniques: Optional[list[str]] = None,
-        detection_fields: Optional[list[ATRDetectionField]] = None,
-        variation_types: Optional[list[ATRVariationType]] = None,
+        categories: list[ATRCategory] | None = None,
+        techniques: list[str] | None = None,
+        detection_fields: list[ATRDetectionField] | None = None,
+        variation_types: list[ATRVariationType] | None = None,
     ) -> None:
         """
         Initialize the ATR dataset loader.
diff --git a/pyrit/datasets/seed_datasets/remote/aya_redteaming_dataset.py b/pyrit/datasets/seed_datasets/remote/aya_redteaming_dataset.py
index 05a905c172..b6bfddd203 100644
--- a/pyrit/datasets/seed_datasets/remote/aya_redteaming_dataset.py
+++ b/pyrit/datasets/seed_datasets/remote/aya_redteaming_dataset.py
@@ -3,7 +3,7 @@
 
 import ast
 import logging
-from typing import Literal, Optional
+from typing import Literal
 
 from pyrit.datasets.seed_datasets.remote.remote_dataset_loader import (
     _RemoteDatasetLoader,
@@ -50,22 +50,21 @@ def __init__(
         language: Literal[
             "English", "Hindi", "French", "Spanish", "Arabic", "Russian", "Serbian", "Tagalog"
         ] = "English",
-        harm_categories: Optional[
-            list[
-                Literal[
-                    "Bullying & Harassment",
-                    "Discrimination & Injustice",
-                    "Graphic material",
-                    "Harms of Representation Allocation and Quality of Service",
-                    "Hate Speech",
-                    "Non-consensual sexual content",
-                    "Profanity",
-                    "Self-Harm",
-                    "Violence, Threats & Incitement",
-                ]
+        harm_categories: list[
+            Literal[
+                "Bullying & Harassment",
+                "Discrimination & Injustice",
+                "Graphic material",
+                "Harms of Representation Allocation and Quality of Service",
+                "Hate Speech",
+                "Non-consensual sexual content",
+                "Profanity",
+                "Self-Harm",
+                "Violence, Threats & Incitement",
             ]
-        ] = None,
-        harm_scope: Optional[Literal["global", "local"]] = None,
+        ]
+        | None = None,
+        harm_scope: Literal["global", "local"] | None = None,
     ) -> None:
         """
         Initialize the Aya Red-teaming dataset loader.
diff --git a/pyrit/datasets/seed_datasets/remote/babelscape_alert_dataset.py b/pyrit/datasets/seed_datasets/remote/babelscape_alert_dataset.py
index 44d9f4c244..2b559f6427 100644
--- a/pyrit/datasets/seed_datasets/remote/babelscape_alert_dataset.py
+++ b/pyrit/datasets/seed_datasets/remote/babelscape_alert_dataset.py
@@ -2,7 +2,7 @@
 # Licensed under the MIT license.
 
 import logging
-from typing import Literal, Optional
+from typing import Literal
 
 from pyrit.datasets.seed_datasets.remote.remote_dataset_loader import (
     _RemoteDatasetLoader,
@@ -32,7 +32,7 @@ def __init__(
         self,
         *,
         source: str = "Babelscape/ALERT",
-        category: Optional[Literal["alert", "alert_adversarial"]] = "alert_adversarial",
+        category: Literal["alert", "alert_adversarial"] | None = "alert_adversarial",
     ) -> None:
         """
         Initialize the Babelscape ALERT dataset loader.
diff --git a/pyrit/datasets/seed_datasets/remote/figstep_dataset.py b/pyrit/datasets/seed_datasets/remote/figstep_dataset.py
index d430a504a4..08e85043c9 100644
--- a/pyrit/datasets/seed_datasets/remote/figstep_dataset.py
+++ b/pyrit/datasets/seed_datasets/remote/figstep_dataset.py
@@ -9,7 +9,7 @@
 import zipfile
 from enum import Enum
 from pathlib import Path
-from typing import Literal, Optional
+from typing import Literal
 
 from pyrit.common.net_utility import make_request_and_raise_if_error_async
 from pyrit.common.path import DB_DATA_PATH
@@ -167,8 +167,8 @@ def __init__(
         *,
         use_tiny: bool = True,
         variant: FigStepVariant = FigStepVariant.FIGSTEP,
-        categories: Optional[list[FigStepCategory]] = None,
-        source: Optional[str] = None,
+        categories: list[FigStepCategory] | None = None,
+        source: str | None = None,
         source_type: Literal["public_url", "file"] = "public_url",
     ) -> None:
         """
@@ -241,8 +241,8 @@ async def fetch_dataset_async(self, *, cache: bool = True) -> SeedDataset:
         required_keys = {"dataset", "category_id", "task_id", "category_name", "question", "instruction"}
         rows = self._fetch_from_url(source=self.source, source_type=self.source_type, cache=cache)
 
-        pro_extract_dir: Optional[Path] = None
-        pro_benign_sentences: Optional[list[str]] = None
+        pro_extract_dir: Path | None = None
+        pro_benign_sentences: list[str] | None = None
         if self.variant == FigStepVariant.FIGSTEP_PRO:
             pro_extract_dir, pro_benign_sentences = await self._ensure_figstep_pro_assets_async(cache=cache)
 
diff --git a/pyrit/datasets/seed_datasets/remote/harmbench_multimodal_dataset.py b/pyrit/datasets/seed_datasets/remote/harmbench_multimodal_dataset.py
index d77767d933..215f1be687 100644
--- a/pyrit/datasets/seed_datasets/remote/harmbench_multimodal_dataset.py
+++ b/pyrit/datasets/seed_datasets/remote/harmbench_multimodal_dataset.py
@@ -4,7 +4,7 @@
 import logging
 import uuid
 from enum import Enum
-from typing import Literal, Optional
+from typing import Literal
 
 from pyrit.datasets.seed_datasets.remote._image_cache import (
     fetch_and_cache_image_async,
@@ -56,7 +56,7 @@ def __init__(
             "harmbench_behaviors_multimodal_all.csv"
         ),
         source_type: Literal["public_url", "file"] = "public_url",
-        categories: Optional[list[SemanticCategory]] = None,
+        categories: list[SemanticCategory] | None = None,
     ) -> None:
         """
         Initialize the HarmBench multimodal dataset loader.
diff --git a/pyrit/datasets/seed_datasets/remote/jailbreakv_28k_dataset.py b/pyrit/datasets/seed_datasets/remote/jailbreakv_28k_dataset.py
index 5ff18a8953..251cfb5405 100644
--- a/pyrit/datasets/seed_datasets/remote/jailbreakv_28k_dataset.py
+++ b/pyrit/datasets/seed_datasets/remote/jailbreakv_28k_dataset.py
@@ -6,7 +6,7 @@
 import uuid
 import zipfile
 from enum import Enum
-from typing import Literal, Optional
+from typing import Literal
 
 from pyrit.datasets.seed_datasets.remote.remote_dataset_loader import (
     _RemoteDatasetLoader,
@@ -87,7 +87,7 @@ def __init__(
         source: str = "JailbreakV-28K/JailBreakV-28k",
         zip_dir: str = str(pathlib.Path.home()),
         split: Literal["JailBreakV_28K", "mini_JailBreakV_28K"] = "mini_JailBreakV_28K",
-        harm_categories: Optional[list[_HarmCategory]] = None,
+        harm_categories: list[_HarmCategory] | None = None,
     ) -> None:
         """
         Initialize the JailBreakV-28K dataset loader.
diff --git a/pyrit/datasets/seed_datasets/remote/jailbreakv_redteam_2k_dataset.py b/pyrit/datasets/seed_datasets/remote/jailbreakv_redteam_2k_dataset.py
index e76b294d83..c4218b82d9 100644
--- a/pyrit/datasets/seed_datasets/remote/jailbreakv_redteam_2k_dataset.py
+++ b/pyrit/datasets/seed_datasets/remote/jailbreakv_redteam_2k_dataset.py
@@ -3,7 +3,6 @@
 
 import logging
 from enum import Enum
-from typing import Optional
 
 from pyrit.datasets.seed_datasets.remote.remote_dataset_loader import (
     _RemoteDatasetLoader,
@@ -77,7 +76,7 @@ def __init__(
         self,
         *,
         source: str = "JailbreakV-28K/JailBreakV-28k",
-        harm_categories: Optional[list[_HarmCategory]] = None,
+        harm_categories: list[_HarmCategory] | None = None,
     ) -> None:
         """
         Initialize the JailBreakV Redteam_2k dataset loader.
diff --git a/pyrit/datasets/seed_datasets/remote/pku_safe_rlhf_dataset.py b/pyrit/datasets/seed_datasets/remote/pku_safe_rlhf_dataset.py
index 01fd374281..38a8cabfb5 100644
--- a/pyrit/datasets/seed_datasets/remote/pku_safe_rlhf_dataset.py
+++ b/pyrit/datasets/seed_datasets/remote/pku_safe_rlhf_dataset.py
@@ -2,7 +2,7 @@
 # Licensed under the MIT license.
 
 import logging
-from typing import Literal, Optional
+from typing import Literal
 
 from pyrit.datasets.seed_datasets.remote.remote_dataset_loader import (
     _RemoteDatasetLoader,
@@ -33,31 +33,30 @@ def __init__(
         *,
         source: str = "PKU-Alignment/PKU-SafeRLHF",
         include_safe_prompts: bool = True,
-        filter_harm_categories: Optional[
-            list[
-                Literal[
-                    "Animal Abuse",
-                    "Copyright Issues",
-                    "Cybercrime",
-                    "Discriminatory Behavior",
-                    "Disrupting Public Order",
-                    "Drugs",
-                    "Economic Crime",
-                    "Endangering National Security",
-                    "Endangering Public Health",
-                    "Environmental Damage",
-                    "Human Trafficking",
-                    "Insulting Behavior",
-                    "Mental Manipulation",
-                    "Physical Harm",
-                    "Privacy Violation",
-                    "Psychological Harm",
-                    "Sexual Content",
-                    "Violence",
-                    "White-Collar Crime",
-                ]
+        filter_harm_categories: list[
+            Literal[
+                "Animal Abuse",
+                "Copyright Issues",
+                "Cybercrime",
+                "Discriminatory Behavior",
+                "Disrupting Public Order",
+                "Drugs",
+                "Economic Crime",
+                "Endangering National Security",
+                "Endangering Public Health",
+                "Environmental Damage",
+                "Human Trafficking",
+                "Insulting Behavior",
+                "Mental Manipulation",
+                "Physical Harm",
+                "Privacy Violation",
+                "Psychological Harm",
+                "Sexual Content",
+                "Violence",
+                "White-Collar Crime",
             ]
-        ] = None,
+        ]
+        | None = None,
     ) -> None:
         """
         Initialize the PKU-SafeRLHF dataset loader.
diff --git a/pyrit/datasets/seed_datasets/remote/promptintel_dataset.py b/pyrit/datasets/seed_datasets/remote/promptintel_dataset.py
index 80998a3af8..cba08eafdb 100644
--- a/pyrit/datasets/seed_datasets/remote/promptintel_dataset.py
+++ b/pyrit/datasets/seed_datasets/remote/promptintel_dataset.py
@@ -5,7 +5,7 @@
 import os
 from datetime import datetime
 from enum import Enum
-from typing import Any, Optional
+from typing import Any
 
 import requests
 
@@ -76,10 +76,10 @@ class _PromptIntelDataset(_RemoteDatasetLoader):
     def __init__(
         self,
         *,
-        api_key: Optional[str] = None,
-        severity: Optional[PromptIntelSeverity] = None,
-        categories: Optional[list[PromptIntelCategory]] = None,
-        search: Optional[str] = None,
+        api_key: str | None = None,
+        severity: PromptIntelSeverity | None = None,
+        categories: list[PromptIntelCategory] | None = None,
+        search: str | None = None,
     ) -> None:
         """
         Initialize the PromptIntel dataset loader.
@@ -139,7 +139,7 @@ def _fetch_all_prompts(self) -> list[dict[str, Any]]:
         }
 
         # Build list of category values to fetch; [None] means fetch all categories
-        categories_to_fetch: list[Optional[str]] = [c.value for c in self._categories] if self._categories else [None]
+        categories_to_fetch: list[str | None] = [c.value for c in self._categories] if self._categories else [None]
 
         all_prompts: list[dict[str, Any]] = []
         seen_ids: set[str] = set()
@@ -187,7 +187,7 @@ def _fetch_all_prompts(self) -> list[dict[str, Any]]:
 
         return all_prompts
 
-    def _parse_datetime(self, date_str: Optional[str]) -> Optional[datetime]:
+    def _parse_datetime(self, date_str: str | None) -> datetime | None:
         """
         Parse an ISO 8601 datetime string from the API.
 
@@ -252,7 +252,7 @@ def _build_metadata(self, record: dict[str, Any]) -> dict[str, str | int]:
 
         return metadata
 
-    def _convert_record_to_seed_prompt(self, record: dict[str, Any]) -> Optional[SeedPrompt]:
+    def _convert_record_to_seed_prompt(self, record: dict[str, Any]) -> SeedPrompt | None:
         """
         Convert a single PromptIntel record into a SeedPrompt.
 
diff --git a/pyrit/datasets/seed_datasets/remote/remote_dataset_loader.py b/pyrit/datasets/seed_datasets/remote/remote_dataset_loader.py
index 0fc9bdd3b9..d536428f69 100644
--- a/pyrit/datasets/seed_datasets/remote/remote_dataset_loader.py
+++ b/pyrit/datasets/seed_datasets/remote/remote_dataset_loader.py
@@ -13,7 +13,7 @@
 from dataclasses import fields
 from enum import Enum
 from pathlib import Path
-from typing import Any, Literal, Optional, TextIO, cast
+from typing import Any, Literal, TextIO, cast
 from urllib.parse import urlparse
 
 import requests
@@ -288,10 +288,10 @@ async def _fetch_from_huggingface_async(
         self,
         *,
         dataset_name: str,
-        config: Optional[str] = None,
-        split: Optional[str] = None,
+        config: str | None = None,
+        split: str | None = None,
         cache: bool = True,
-        token: Optional[str] = None,
+        token: str | None = None,
         **kwargs: Any,
     ) -> Any:
         """
@@ -356,7 +356,7 @@ def _load_dataset_sync() -> Any:
             logger.error(f"Failed to load HuggingFace dataset {dataset_name}: {e}")
             raise
 
-    async def _parse_metadata_async(self) -> Optional[SeedDatasetMetadata]:
+    async def _parse_metadata_async(self) -> SeedDatasetMetadata | None:
         """
         Extract metadata from class attributes, wrap in sets, and format into SeedDatasetMetadata.
 
@@ -423,7 +423,7 @@ async def _fetch_zip_from_url_async(
 
         def _download_and_parse() -> dict[str, list[dict[str, Any]]]:
             zip_path: Path
-            temp_to_clean: Optional[Path] = None
+            temp_to_clean: Path | None = None
             if cache and cache_path.exists():
                 zip_path = cache_path
             else:
diff --git a/pyrit/datasets/seed_datasets/remote/siuo_dataset.py b/pyrit/datasets/seed_datasets/remote/siuo_dataset.py
index 1a95fe9d5e..5e14c03049 100644
--- a/pyrit/datasets/seed_datasets/remote/siuo_dataset.py
+++ b/pyrit/datasets/seed_datasets/remote/siuo_dataset.py
@@ -4,7 +4,7 @@
 import logging
 import uuid
 from enum import Enum
-from typing import Literal, Optional
+from typing import Literal
 
 from pyrit.datasets.seed_datasets.remote._image_cache import (
     fetch_and_cache_image_async,
@@ -110,7 +110,7 @@ def __init__(
         *,
         source: str = GEN_JSON_URL,
         source_type: Literal["public_url", "file"] = "public_url",
-        categories: Optional[list[SIUOCategory]] = None,
+        categories: list[SIUOCategory] | None = None,
     ) -> None:
         """
         Initialize the SIUO dataset loader.
diff --git a/pyrit/datasets/seed_datasets/remote/sorry_bench_dataset.py b/pyrit/datasets/seed_datasets/remote/sorry_bench_dataset.py
index 241b4cc7ff..e9c6936288 100644
--- a/pyrit/datasets/seed_datasets/remote/sorry_bench_dataset.py
+++ b/pyrit/datasets/seed_datasets/remote/sorry_bench_dataset.py
@@ -3,7 +3,6 @@
 
 import logging
 import os
-from typing import Optional
 
 from pyrit.datasets.seed_datasets.remote.remote_dataset_loader import (
     _RemoteDatasetLoader,
@@ -103,9 +102,9 @@ def __init__(
         self,
         *,
         source: str = "sorry-bench/sorry-bench-202503",
-        categories: Optional[list[str]] = None,
-        prompt_style: Optional[str] = None,
-        token: Optional[str] = None,
+        categories: list[str] | None = None,
+        prompt_style: str | None = None,
+        token: str | None = None,
     ) -> None:
         """
         Initialize the Sorry-Bench dataset loader.
diff --git a/pyrit/datasets/seed_datasets/remote/visual_leak_bench_dataset.py b/pyrit/datasets/seed_datasets/remote/visual_leak_bench_dataset.py
index 31e11769cd..b32026e921 100644
--- a/pyrit/datasets/seed_datasets/remote/visual_leak_bench_dataset.py
+++ b/pyrit/datasets/seed_datasets/remote/visual_leak_bench_dataset.py
@@ -4,7 +4,7 @@
 import logging
 import uuid
 from enum import Enum
-from typing import Literal, Optional
+from typing import Literal
 
 from pyrit.datasets.seed_datasets.remote._image_cache import (
     fetch_and_cache_image_async,
@@ -82,8 +82,8 @@ def __init__(
         *,
         source: str = METADATA_URL,
         source_type: Literal["public_url", "file"] = "public_url",
-        categories: Optional[list[VisualLeakBenchCategory]] = None,
-        pii_types: Optional[list[VisualLeakBenchPIIType]] = None,
+        categories: list[VisualLeakBenchCategory] | None = None,
+        pii_types: list[VisualLeakBenchPIIType] | None = None,
     ) -> None:
         """
         Initialize the VisualLeakBench dataset loader.
diff --git a/pyrit/datasets/seed_datasets/remote/vlsu_multimodal_dataset.py b/pyrit/datasets/seed_datasets/remote/vlsu_multimodal_dataset.py
index 26a2460afb..a52b339ea4 100644
--- a/pyrit/datasets/seed_datasets/remote/vlsu_multimodal_dataset.py
+++ b/pyrit/datasets/seed_datasets/remote/vlsu_multimodal_dataset.py
@@ -4,7 +4,7 @@
 import logging
 import uuid
 from enum import Enum
-from typing import Literal, Optional
+from typing import Literal
 
 from pyrit.datasets.seed_datasets.remote._image_cache import (
     fetch_and_cache_image_async,
@@ -62,9 +62,9 @@ def __init__(
         *,
         source: str = "https://raw.githubusercontent.com/apple/ml-vlsu/main/data/VLSU.csv",
         source_type: Literal["public_url", "file"] = "public_url",
-        categories: Optional[list[VLSUCategory]] = None,
-        unsafe_grades: Optional[list[str]] = None,
-        max_examples: Optional[int] = None,
+        categories: list[VLSUCategory] | None = None,
+        unsafe_grades: list[str] | None = None,
+        max_examples: int | None = None,
     ) -> None:
         """
         Initialize the ML-VLSU multimodal dataset loader.
diff --git a/pyrit/datasets/seed_datasets/seed_dataset_provider.py b/pyrit/datasets/seed_datasets/seed_dataset_provider.py
index 3e27d9e051..56714e2a94 100644
--- a/pyrit/datasets/seed_datasets/seed_dataset_provider.py
+++ b/pyrit/datasets/seed_datasets/seed_dataset_provider.py
@@ -6,7 +6,7 @@
 import logging
 from abc import ABC, abstractmethod
 from dataclasses import fields as dc_fields
-from typing import Any, Optional
+from typing import Any
 
 from tqdm import tqdm
 
@@ -120,7 +120,7 @@ async def fetch_dataset(self, *, cache: bool = True) -> SeedDataset:  # pyrit-as
         )
         return await self.fetch_dataset_async(cache=cache)
 
-    async def _parse_metadata_async(self) -> Optional[SeedDatasetMetadata]:
+    async def _parse_metadata_async(self) -> SeedDatasetMetadata | None:
         """
         Parse provider-specific metadata into the shared schema.
 
@@ -144,7 +144,7 @@ def get_all_providers(cls) -> dict[str, type["SeedDatasetProvider"]]:
         return cls._registry.copy()
 
     @classmethod
-    async def get_all_dataset_names_async(cls, filters: Optional[SeedDatasetFilter] = None) -> list[str]:
+    async def get_all_dataset_names_async(cls, filters: SeedDatasetFilter | None = None) -> list[str]:
         """
         Get the names of all registered datasets.
 
@@ -273,7 +273,7 @@ def _match_single_criterion(
     async def fetch_datasets_async(
         cls,
         *,
-        dataset_names: Optional[list[str]] = None,
+        dataset_names: list[str] | None = None,
         cache: bool = True,
         max_concurrency: int = 5,
     ) -> list[SeedDataset]:
@@ -315,7 +315,7 @@ async def fetch_datasets_async(
 
         async def fetch_single_dataset_async(
             provider_name: str, provider_class: type["SeedDatasetProvider"]
-        ) -> Optional[tuple[str, SeedDataset]]:
+        ) -> tuple[str, SeedDataset] | None:
             """
             Fetch a single dataset with error handling.
 
@@ -341,7 +341,7 @@ async def fetch_single_dataset_async(
 
         async def fetch_with_semaphore_async(
             provider_name: str, provider_class: type["SeedDatasetProvider"]
-        ) -> Optional[tuple[str, SeedDataset]]:
+        ) -> tuple[str, SeedDataset] | None:
             """
             Enforce concurrency limit and update progress during dataset fetch.
 
diff --git a/pyrit/datasets/seed_datasets/seed_metadata.py b/pyrit/datasets/seed_datasets/seed_metadata.py
index 7b40b95a6b..cdd1149a85 100644
--- a/pyrit/datasets/seed_datasets/seed_metadata.py
+++ b/pyrit/datasets/seed_datasets/seed_metadata.py
@@ -4,7 +4,7 @@
 import logging
 from dataclasses import dataclass, fields
 from enum import Enum
-from typing import Any, ClassVar, Literal, Optional
+from typing import Any, ClassVar, Literal
 
 logger = logging.getLogger(__name__)
 
@@ -94,12 +94,12 @@ class SeedDatasetMetadata:
     # All fields are optional sets to support both real metadata (single-element)
     # and filter criteria (multi-element). SINGULAR_FIELDS enforces that parsers
     # only produce single-element sets for size and source_type.
-    tags: Optional[set[str]] = None
-    size: Optional[set[str]] = None
-    modalities: Optional[set[str]] = None
-    source_type: Optional[set[str]] = None
-    load_time: Optional[set[SeedDatasetLoadTime]] = None
-    harm_categories: Optional[set[str]] = None
+    tags: set[str] | None = None
+    size: set[str] | None = None
+    modalities: set[str] | None = None
+    source_type: set[str] | None = None
+    load_time: set[SeedDatasetLoadTime] | None = None
+    harm_categories: set[str] | None = None
 
     # Fields that must have at most 1 element in real dataset metadata.
     SINGULAR_FIELDS: ClassVar[frozenset[str]] = frozenset({"size", "source_type"})
@@ -195,7 +195,7 @@ class SeedDatasetFilter:
     def __init__(
         self,
         *,
-        criteria: Optional[list[SeedDatasetMetadata]] = None,
+        criteria: list[SeedDatasetMetadata] | None = None,
         strict_match: bool = False,
         **kwargs: Any,
     ) -> None:
diff --git a/pyrit/embedding/openai_text_embedding.py b/pyrit/embedding/openai_text_embedding.py
index 5efbb69107..86a774c404 100644
--- a/pyrit/embedding/openai_text_embedding.py
+++ b/pyrit/embedding/openai_text_embedding.py
@@ -3,7 +3,7 @@
 
 import asyncio
 from collections.abc import Awaitable, Callable
-from typing import Any, Optional
+from typing import Any
 
 import tenacity
 from openai import AsyncOpenAI
@@ -31,9 +31,9 @@ class OpenAITextEmbedding(EmbeddingSupport):
     def __init__(
         self,
         *,
-        api_key: Optional[str | Callable[[], str | Awaitable[str]]] = None,
-        endpoint: Optional[str] = None,
-        model_name: Optional[str] = None,
+        api_key: str | Callable[[], str | Awaitable[str]] | None = None,
+        endpoint: str | None = None,
+        model_name: str | None = None,
     ) -> None:
         """
         Initialize text embedding client for Azure OpenAI or platform OpenAI.
diff --git a/pyrit/exceptions/exception_classes.py b/pyrit/exceptions/exception_classes.py
index b402499e98..b5e71bbfe3 100644
--- a/pyrit/exceptions/exception_classes.py
+++ b/pyrit/exceptions/exception_classes.py
@@ -6,7 +6,7 @@
 import os
 from abc import ABC
 from collections.abc import Callable
-from typing import Any, Optional
+from typing import Any
 
 from openai import RateLimitError
 from tenacity import (
@@ -176,7 +176,7 @@ def __init__(self, *, status_code: int = 429, message: str = "Rate Limit Excepti
 class ServerErrorException(PyritException):
     """Exception class for opaque 5xx errors returned by the server."""
 
-    def __init__(self, *, status_code: int = 500, message: str = "Server Error", body: Optional[str] = None) -> None:
+    def __init__(self, *, status_code: int = 500, message: str = "Server Error", body: str | None = None) -> None:
         """
         Initialize a server error exception.
 
@@ -247,7 +247,7 @@ class ExperimentalWarning(FutureWarning):
 
 
 def pyrit_custom_result_retry(
-    retry_function: Callable[..., bool], retry_max_num_attempts: Optional[int] = None
+    retry_function: Callable[..., bool], retry_max_num_attempts: int | None = None
 ) -> Callable[..., Any]:
     """
     Apply retry logic with exponential backoff to a function.
diff --git a/pyrit/exceptions/exception_context.py b/pyrit/exceptions/exception_context.py
index 9b45ac8737..7ee3a0ccce 100644
--- a/pyrit/exceptions/exception_context.py
+++ b/pyrit/exceptions/exception_context.py
@@ -13,7 +13,7 @@
 from contextvars import ContextVar
 from dataclasses import dataclass, field
 from enum import Enum
-from typing import Any, Optional
+from typing import Any
 
 from pyrit.models import ComponentIdentifier
 
@@ -59,25 +59,25 @@ class ExecutionContext:
     component_role: ComponentRole = ComponentRole.UNKNOWN
 
     # The attack strategy class name (e.g., "PromptSendingAttack")
-    attack_strategy_name: Optional[str] = None
+    attack_strategy_name: str | None = None
 
     # The identifier for the attack strategy
-    attack_identifier: Optional[ComponentIdentifier] = None
+    attack_identifier: ComponentIdentifier | None = None
 
     # The identifier from the component's get_identifier() (target, scorer, etc.)
-    component_identifier: Optional[ComponentIdentifier] = None
+    component_identifier: ComponentIdentifier | None = None
 
     # The objective target conversation ID if available
-    objective_target_conversation_id: Optional[str] = None
+    objective_target_conversation_id: str | None = None
 
     # The endpoint/URI if available (extracted from component_identifier for quick access)
-    endpoint: Optional[str] = None
+    endpoint: str | None = None
 
     # The component class name (extracted from component_identifier.__type__ for quick access)
-    component_name: Optional[str] = None
+    component_name: str | None = None
 
     # The attack objective if available
-    objective: Optional[str] = None
+    objective: str | None = None
 
     def get_retry_context_string(self) -> str:
         """
@@ -135,10 +135,10 @@ def get_exception_details(self) -> str:
 
 
 # The contextvar that stores the current execution context
-_execution_context: ContextVar[Optional[ExecutionContext]] = ContextVar("execution_context", default=None)
+_execution_context: ContextVar[ExecutionContext | None] = ContextVar("execution_context", default=None)
 
 
-def get_execution_context() -> Optional[ExecutionContext]:
+def get_execution_context() -> ExecutionContext | None:
     """
     Get the current execution context.
 
@@ -213,11 +213,11 @@ def __exit__(self, exc_type: Any, exc_val: Any, exc_tb: Any) -> None:
 def execution_context(
     *,
     component_role: ComponentRole,
-    attack_strategy_name: Optional[str] = None,
-    attack_identifier: Optional[ComponentIdentifier] = None,
-    component_identifier: Optional[ComponentIdentifier] = None,
-    objective_target_conversation_id: Optional[str] = None,
-    objective: Optional[str] = None,
+    attack_strategy_name: str | None = None,
+    attack_identifier: ComponentIdentifier | None = None,
+    component_identifier: ComponentIdentifier | None = None,
+    objective_target_conversation_id: str | None = None,
+    objective: str | None = None,
 ) -> ExecutionContextManager:
     """
     Create an execution context manager with the specified parameters.
diff --git a/pyrit/executor/attack/component/conversation_manager.py b/pyrit/executor/attack/component/conversation_manager.py
index b7d554775c..164ca74e11 100644
--- a/pyrit/executor/attack/component/conversation_manager.py
+++ b/pyrit/executor/attack/component/conversation_manager.py
@@ -56,7 +56,7 @@ def get_adversarial_chat_messages(
     adversarial_chat_conversation_id: str,
     attack_identifier: ComponentIdentifier,
     adversarial_chat_target_identifier: ComponentIdentifier,
-    labels: Optional[dict[str, str]] = None,  # deprecated
+    labels: dict[str, str] | None = None,  # deprecated
 ) -> list[Message]:
     """
     Transform prepended conversation messages for adversarial chat with swapped roles.
@@ -146,7 +146,7 @@ async def build_conversation_context_string_async(messages: list[Message]) -> st
     return await normalizer.normalize_string_async(messages)
 
 
-def get_prepended_turn_count(prepended_conversation: Optional[list[Message]]) -> int:
+def get_prepended_turn_count(prepended_conversation: list[Message] | None) -> int:
     """
     Count the number of turns (assistant responses) in a prepended conversation.
 
@@ -191,7 +191,7 @@ def __init__(
         self,
         *,
         attack_identifier: ComponentIdentifier,
-        prompt_normalizer: Optional[PromptNormalizer] = None,
+        prompt_normalizer: PromptNormalizer | None = None,
     ) -> None:
         """
         Initialize the conversation manager.
@@ -219,9 +219,7 @@ def get_conversation(self, conversation_id: str) -> list[Message]:
         conversation = self._memory.get_conversation(conversation_id=conversation_id)
         return list(conversation)
 
-    def get_last_message(
-        self, *, conversation_id: str, role: Optional[ChatMessageRole] = None
-    ) -> Optional[MessagePiece]:
+    def get_last_message(self, *, conversation_id: str, role: ChatMessageRole | None = None) -> MessagePiece | None:
         """
         Retrieve the most recent message from a conversation.
 
@@ -251,7 +249,7 @@ def set_system_prompt(
         target: PromptTarget,
         conversation_id: str,
         system_prompt: str,
-        labels: Optional[dict[str, str]] = None,  # deprecated
+        labels: dict[str, str] | None = None,  # deprecated
     ) -> None:
         """
         Set or update the system prompt for a conversation.
@@ -288,10 +286,10 @@ async def initialize_context_async(
         context: "AttackContext[Any]",
         target: PromptTarget,
         conversation_id: str,
-        request_converters: Optional[list[PromptConverterConfiguration]] = None,
+        request_converters: list[PromptConverterConfiguration] | None = None,
         prepended_conversation_config: Optional["PrependedConversationConfig"] = None,
-        max_turns: Optional[int] = None,
-        memory_labels: Optional[dict[str, str]] = None,
+        max_turns: int | None = None,
+        memory_labels: dict[str, str] | None = None,
     ) -> ConversationState:
         """
         Initialize attack context with prepended conversation and merged labels.
@@ -438,9 +436,9 @@ async def add_prepended_conversation_to_memory_async(
         *,
         prepended_conversation: list[Message],
         conversation_id: str,
-        request_converters: Optional[list[PromptConverterConfiguration]] = None,
+        request_converters: list[PromptConverterConfiguration] | None = None,
         prepended_conversation_config: Optional["PrependedConversationConfig"] = None,
-        max_turns: Optional[int] = None,
+        max_turns: int | None = None,
     ) -> int:
         """
         Add prepended conversation messages to memory for a chat target.
@@ -519,9 +517,9 @@ async def _process_prepended_for_chat_target_async(
         context: "AttackContext[Any]",
         prepended_conversation: list[Message],
         conversation_id: str,
-        request_converters: Optional[list[PromptConverterConfiguration]],
+        request_converters: list[PromptConverterConfiguration] | None,
         prepended_conversation_config: Optional["PrependedConversationConfig"],
-        max_turns: Optional[int],
+        max_turns: int | None,
     ) -> ConversationState:
         """
         Process prepended conversation for a chat target.
@@ -587,7 +585,7 @@ async def _apply_converters_async(
         *,
         message: Message,
         request_converters: list[PromptConverterConfiguration],
-        apply_to_roles: Optional[list[ChatMessageRole]],
+        apply_to_roles: list[ChatMessageRole] | None,
     ) -> None:
         """
         Apply converters to message pieces.
diff --git a/pyrit/executor/attack/compound/sequential_attack.py b/pyrit/executor/attack/compound/sequential_attack.py
index 7e851507d4..15e6eb1dc3 100644
--- a/pyrit/executor/attack/compound/sequential_attack.py
+++ b/pyrit/executor/attack/compound/sequential_attack.py
@@ -26,7 +26,7 @@
 from dataclasses import dataclass, field
 from datetime import datetime, timezone
 from enum import Enum
-from typing import TYPE_CHECKING, Any, Optional
+from typing import TYPE_CHECKING, Any
 
 from pydantic import Field
 
@@ -107,8 +107,8 @@ class SequentialChildAttack:
 
     strategy: AttackStrategy[Any, AttackResult]
     seed_group: SeedAttackGroup
-    adversarial_chat: Optional[PromptTarget] = None
-    objective_scorer: Optional[TrueFalseScorer] = None
+    adversarial_chat: PromptTarget | None = None
+    objective_scorer: TrueFalseScorer | None = None
     memory_labels: Mapping[str, str] = field(default_factory=dict)
 
 
@@ -288,7 +288,7 @@ async def _run_child_attack_async(
         *,
         child_attack: SequentialChildAttack,
         memory_labels: dict[str, str],
-        attribution: Optional[AttackResultAttribution] = None,
+        attribution: AttackResultAttribution | None = None,
     ) -> AttackResult:
         """
         Execute one child attack via ``AttackExecutor`` and return its result.
diff --git a/pyrit/executor/attack/core/attack_config.py b/pyrit/executor/attack/core/attack_config.py
index c86131f769..803c6c4296 100644
--- a/pyrit/executor/attack/core/attack_config.py
+++ b/pyrit/executor/attack/core/attack_config.py
@@ -3,7 +3,6 @@
 
 from dataclasses import dataclass, field
 from pathlib import Path
-from typing import Optional, Union
 
 from pyrit.executor.core import StrategyConverterConfig
 from pyrit.models import SeedPrompt
@@ -26,10 +25,10 @@ class AttackAdversarialConfig:
     target: PromptTarget
 
     # Path to the YAML file containing the system prompt for the adversarial chat target
-    system_prompt_path: Optional[Union[str, Path]] = None
+    system_prompt_path: str | Path | None = None
 
     # Seed prompt for the adversarial chat target (supports {{ objective }} template variable)
-    seed_prompt: Union[str, SeedPrompt] = "Generate your first message to achieve: {{ objective }}"
+    seed_prompt: str | SeedPrompt = "Generate your first message to achieve: {{ objective }}"
 
 
 @dataclass
@@ -42,10 +41,10 @@ class AttackScoringConfig:
     """
 
     # Primary scorer for evaluating attack effectiveness
-    objective_scorer: Optional[TrueFalseScorer] = None
+    objective_scorer: TrueFalseScorer | None = None
 
     # Refusal scorer for detecting refusals or non-compliance
-    refusal_scorer: Optional[TrueFalseScorer] = None
+    refusal_scorer: TrueFalseScorer | None = None
 
     # Additional scorers for auxiliary metrics or custom evaluations
     auxiliary_scorers: list[Scorer] = field(default_factory=list)
diff --git a/pyrit/executor/attack/core/attack_executor.py b/pyrit/executor/attack/core/attack_executor.py
index 88c2108b8b..4f3ecb2cbe 100644
--- a/pyrit/executor/attack/core/attack_executor.py
+++ b/pyrit/executor/attack/core/attack_executor.py
@@ -145,8 +145,8 @@ def __init__(self, *, max_concurrency: int = 1) -> None:
         # and then run it under more than one ``asyncio.run(...)`` invocation. By
         # constructing the semaphore inside ``_get_semaphore()`` and rebuilding when the
         # running loop changes, one AttackExecutor instance is safe to reuse across loops.
-        self._semaphore: Optional[asyncio.Semaphore] = None
-        self._semaphore_loop: Optional[asyncio.AbstractEventLoop] = None
+        self._semaphore: asyncio.Semaphore | None = None
+        self._semaphore_loop: asyncio.AbstractEventLoop | None = None
 
     def _get_semaphore(self) -> asyncio.Semaphore:
         """
@@ -174,9 +174,9 @@ async def execute_attack_from_seed_groups_async(
         seed_groups: Sequence[SeedAttackGroup],
         adversarial_chat: Optional["PromptTarget"] = None,
         objective_scorer: Optional["TrueFalseScorer"] = None,
-        field_overrides: Optional[Sequence[dict[str, Any]]] = None,
+        field_overrides: Sequence[dict[str, Any]] | None = None,
         return_partial_on_failure: bool = False,
-        attribution: Optional[AttackResultAttribution] = None,
+        attribution: AttackResultAttribution | None = None,
         **broadcast_fields: Any,
     ) -> AttackExecutorResult[AttackStrategyResultT]:
         """
@@ -254,9 +254,9 @@ async def execute_attack_async(
         *,
         attack: AttackStrategy[AttackStrategyContextT, AttackStrategyResultT],
         objectives: Sequence[str],
-        field_overrides: Optional[Sequence[dict[str, Any]]] = None,
+        field_overrides: Sequence[dict[str, Any]] | None = None,
         return_partial_on_failure: bool = False,
-        attribution: Optional[AttackResultAttribution] = None,
+        attribution: AttackResultAttribution | None = None,
         **broadcast_fields: Any,
     ) -> AttackExecutorResult[AttackStrategyResultT]:
         """
@@ -323,7 +323,7 @@ async def _execute_with_params_list_async(
         attack: AttackStrategy[AttackStrategyContextT, AttackStrategyResultT],
         params_list: Sequence[AttackParameters],
         return_partial_on_failure: bool = False,
-        attribution: Optional[AttackResultAttribution] = None,
+        attribution: AttackResultAttribution | None = None,
     ) -> AttackExecutorResult[AttackStrategyResultT]:
         """
         Execute attacks in parallel with a list of pre-built parameters.
diff --git a/pyrit/executor/attack/core/attack_parameters.py b/pyrit/executor/attack/core/attack_parameters.py
index 72739c59ed..7ce2cdecee 100644
--- a/pyrit/executor/attack/core/attack_parameters.py
+++ b/pyrit/executor/attack/core/attack_parameters.py
@@ -5,7 +5,7 @@
 
 import dataclasses
 from dataclasses import dataclass, field
-from typing import TYPE_CHECKING, Any, Optional, TypeVar
+from typing import TYPE_CHECKING, Any, TypeVar
 
 from pyrit.models import Message, SeedAttackGroup, SeedGroup
 
@@ -33,13 +33,13 @@ class AttackParameters:
     objective: str
 
     # Optional message to send to the objective target (overrides objective if provided)
-    next_message: Optional[Message] = None
+    next_message: Message | None = None
 
     # Conversation that is automatically prepended to the target model
-    prepended_conversation: Optional[list[Message]] = None
+    prepended_conversation: list[Message] | None = None
 
     # Additional labels that can be applied to the prompts throughout the attack
-    memory_labels: Optional[dict[str, str]] = field(default_factory=dict)
+    memory_labels: dict[str, str] | None = field(default_factory=dict)
 
     def __str__(self) -> str:
         """Return a nicely formatted string representation of the attack parameters."""
@@ -78,8 +78,8 @@ async def from_seed_group_async(
         cls: type[AttackParamsT],
         *,
         seed_group: SeedAttackGroup,
-        adversarial_chat: Optional[PromptTarget] = None,
-        objective_scorer: Optional[TrueFalseScorer] = None,
+        adversarial_chat: PromptTarget | None = None,
+        objective_scorer: TrueFalseScorer | None = None,
         **overrides: Any,
     ) -> AttackParamsT:
         """
diff --git a/pyrit/executor/attack/core/attack_strategy.py b/pyrit/executor/attack/core/attack_strategy.py
index 887a467a10..2a2ac9f022 100644
--- a/pyrit/executor/attack/core/attack_strategy.py
+++ b/pyrit/executor/attack/core/attack_strategy.py
@@ -10,7 +10,7 @@
 import uuid
 from abc import ABC
 from dataclasses import dataclass, field
-from typing import TYPE_CHECKING, Any, ClassVar, Generic, Optional, TypeVar, Union, overload
+from typing import TYPE_CHECKING, Any, ClassVar, Generic, TypeVar, overload
 
 from pyrit.common.logger import logger
 from pyrit.exceptions.retry_collector import (
@@ -68,16 +68,16 @@ class AttackContext(StrategyContext, ABC, Generic[AttackParamsT]):
     related_conversations: set[ConversationReference] = field(default_factory=set)
 
     # Mutable overrides for attacks that generate these values internally
-    _next_message_override: Optional[Message] = None
-    _prepended_conversation_override: Optional[list[Message]] = None
-    _memory_labels_override: Optional[dict[str, str]] = None
+    _next_message_override: Message | None = None
+    _prepended_conversation_override: list[Message] | None = None
+    _memory_labels_override: dict[str, str] | None = None
 
     # Optional attribution from an upstream orchestrator (e.g. Scenario). When
     # set, the persistence path stamps attribution_parent_id + attribution_data
     # onto the resulting AttackResult so it can be located later for hydration
     # and resume. Set by AttackExecutor per-task before scheduling. Stays None
     # for ad-hoc/direct attack execution outside any orchestrator.
-    _attribution: Optional[AttackResultAttribution] = None
+    _attribution: AttackResultAttribution | None = None
 
     # Convenience properties that delegate to params or overrides
     @property
@@ -115,7 +115,7 @@ def prepended_conversation(self, value: list[Message]) -> None:
         self._prepended_conversation_override = value
 
     @property
-    def next_message(self) -> Optional[Message]:
+    def next_message(self) -> Message | None:
         """Optional message to send to the objective target."""
         # Check override first (for attacks that generate internally)
         if self._next_message_override is not None:
@@ -126,7 +126,7 @@ def next_message(self) -> Optional[Message]:
         return None
 
     @next_message.setter
-    def next_message(self, value: Optional[Message]) -> None:
+    def next_message(self, value: Message | None) -> None:
         """Set the next message (for attacks that generate internally)."""
         self._next_message_override = value
 
@@ -392,8 +392,8 @@ def __init__(
     def _create_identifier(
         self,
         *,
-        params: Optional[dict[str, Any]] = None,
-        children: Optional[dict[str, Union[ComponentIdentifier, list[ComponentIdentifier]]]] = None,
+        params: dict[str, Any] | None = None,
+        children: dict[str, ComponentIdentifier | list[ComponentIdentifier]] | None = None,
     ) -> ComponentIdentifier:
         """
         Construct the attack strategy identifier.
@@ -411,7 +411,7 @@ def _create_identifier(
         Returns:
             ComponentIdentifier: The identifier for this attack strategy.
         """
-        all_children: dict[str, Union[ComponentIdentifier, list[ComponentIdentifier]]] = {
+        all_children: dict[str, ComponentIdentifier | list[ComponentIdentifier]] = {
             "objective_target": self.get_objective_target().get_identifier(),
         }
 
@@ -468,7 +468,7 @@ def get_objective_target(self) -> PromptTarget:
         """
         return self._objective_target
 
-    def get_attack_scoring_config(self) -> Optional[AttackScoringConfig]:
+    def get_attack_scoring_config(self) -> AttackScoringConfig | None:
         """
         Get the attack scoring configuration used by this strategy.
 
@@ -495,9 +495,9 @@ async def execute_async(
         self,
         *,
         objective: str,
-        next_message: Optional[Message] = None,
-        prepended_conversation: Optional[list[Message]] = None,
-        memory_labels: Optional[dict[str, str]] = None,
+        next_message: Message | None = None,
+        prepended_conversation: list[Message] | None = None,
+        memory_labels: dict[str, str] | None = None,
         **kwargs: Any,
     ) -> AttackStrategyResultT: ...
 
diff --git a/pyrit/executor/attack/multi_turn/chunked_request.py b/pyrit/executor/attack/multi_turn/chunked_request.py
index 6289b39841..b0ec80118f 100644
--- a/pyrit/executor/attack/multi_turn/chunked_request.py
+++ b/pyrit/executor/attack/multi_turn/chunked_request.py
@@ -5,7 +5,7 @@
 import textwrap
 from dataclasses import dataclass, field
 from string import Formatter
-from typing import TYPE_CHECKING, Any, Optional
+from typing import TYPE_CHECKING, Any
 
 from pyrit.common.apply_defaults import REQUIRED_VALUE, apply_defaults
 from pyrit.exceptions import ComponentRole, execution_context
@@ -102,9 +102,9 @@ def __init__(
         total_length: int = 200,
         chunk_type: str = "characters",
         request_template: str = DEFAULT_TEMPLATE,
-        attack_converter_config: Optional[AttackConverterConfig] = None,
-        attack_scoring_config: Optional[AttackScoringConfig] = None,
-        prompt_normalizer: Optional[PromptNormalizer] = None,
+        attack_converter_config: AttackConverterConfig | None = None,
+        attack_scoring_config: AttackScoringConfig | None = None,
+        prompt_normalizer: PromptNormalizer | None = None,
     ) -> None:
         """
         Initialize the chunked request attack strategy.
@@ -167,7 +167,7 @@ def __init__(
         attack_scoring_config = attack_scoring_config or AttackScoringConfig()
 
         self._auxiliary_scorers = attack_scoring_config.auxiliary_scorers
-        self._objective_scorer: Optional[TrueFalseScorer] = attack_scoring_config.objective_scorer
+        self._objective_scorer: TrueFalseScorer | None = attack_scoring_config.objective_scorer
 
         # Initialize prompt normalizer and conversation manager
         self._prompt_normalizer = prompt_normalizer or PromptNormalizer()
@@ -176,7 +176,7 @@ def __init__(
             prompt_normalizer=self._prompt_normalizer,
         )
 
-    def get_attack_scoring_config(self) -> Optional[AttackScoringConfig]:
+    def get_attack_scoring_config(self) -> AttackScoringConfig | None:
         """
         Get the attack scoring configuration used by this strategy.
 
@@ -333,8 +333,8 @@ async def _perform_async(self, *, context: ChunkedRequestAttackContext) -> Attac
     def _determine_attack_outcome(
         self,
         *,
-        score: Optional[Score],
-    ) -> tuple[AttackOutcome, Optional[str]]:
+        score: Score | None,
+    ) -> tuple[AttackOutcome, str | None]:
         """
         Determine the outcome of the attack based on the score.
 
@@ -359,7 +359,7 @@ async def _score_combined_value_async(
         *,
         combined_value: str,
         objective: str,
-    ) -> Optional[Score]:
+    ) -> Score | None:
         """
         Score the combined chunk responses against the objective.
 
diff --git a/pyrit/executor/attack/multi_turn/crescendo.py b/pyrit/executor/attack/multi_turn/crescendo.py
index a241affa66..ab578cc668 100644
--- a/pyrit/executor/attack/multi_turn/crescendo.py
+++ b/pyrit/executor/attack/multi_turn/crescendo.py
@@ -8,7 +8,7 @@
 import re
 from dataclasses import dataclass
 from pathlib import Path
-from typing import TYPE_CHECKING, Any, Optional, Union, cast
+from typing import TYPE_CHECKING, Any, cast
 
 from pyrit.common.apply_defaults import REQUIRED_VALUE, apply_defaults
 from pyrit.common.path import EXECUTOR_SEED_PROMPT_PATH
@@ -75,7 +75,7 @@ class CrescendoAttackContext(MultiTurnAttackContext[Any]):
     """Context for the Crescendo attack strategy."""
 
     # Text that was refused by the target in the previous attempt (used for backtracking)
-    refused_text: Optional[str] = None
+    refused_text: str | None = None
 
     # Counter for number of backtracks performed during the attack
     backtrack_count: int = 0
@@ -144,12 +144,12 @@ def __init__(
         *,
         objective_target: PromptTarget = REQUIRED_VALUE,  # type: ignore[ty:invalid-parameter-default]
         attack_adversarial_config: AttackAdversarialConfig,
-        attack_converter_config: Optional[AttackConverterConfig] = None,
-        attack_scoring_config: Optional[AttackScoringConfig] = None,
-        prompt_normalizer: Optional[PromptNormalizer] = None,
+        attack_converter_config: AttackConverterConfig | None = None,
+        attack_scoring_config: AttackScoringConfig | None = None,
+        prompt_normalizer: PromptNormalizer | None = None,
         max_backtracks: int = 10,
         max_turns: int = 10,
-        prepended_conversation_config: Optional[PrependedConversationConfig] = None,
+        prepended_conversation_config: PrependedConversationConfig | None = None,
     ) -> None:
         """
         Initialize the Crescendo attack strategy.
@@ -249,7 +249,7 @@ def __init__(
         # Store the prepended conversation configuration
         self._prepended_conversation_config = prepended_conversation_config
 
-    def get_attack_scoring_config(self) -> Optional[AttackScoringConfig]:
+    def get_attack_scoring_config(self) -> AttackScoringConfig | None:
         """
         Get the attack scoring configuration used by this strategy.
 
@@ -315,7 +315,7 @@ async def _setup_async(self, *, context: CrescendoAttackContext) -> None:
         )
 
         # Set up adversarial chat with prepended conversation
-        adversarial_chat_context: Optional[str] = None
+        adversarial_chat_context: str | None = None
         if context.prepended_conversation:
             # Build context string for system prompt
             normalizer = ConversationContextNormalizer()
@@ -760,7 +760,7 @@ async def _backtrack_memory_async(self, *, conversation_id: str) -> str:
         self._logger.debug(f"Backtracked conversation from {conversation_id} to {new_conversation_id}")
         return new_conversation_id
 
-    def _set_adversarial_chat_system_prompt_template(self, *, system_prompt_template_path: Union[Path, str]) -> None:
+    def _set_adversarial_chat_system_prompt_template(self, *, system_prompt_template_path: Path | str) -> None:
         """
         Set the system prompt template for the adversarial chat.
 
diff --git a/pyrit/executor/attack/multi_turn/multi_prompt_sending.py b/pyrit/executor/attack/multi_turn/multi_prompt_sending.py
index 2c4255984b..5a92e9cf10 100644
--- a/pyrit/executor/attack/multi_turn/multi_prompt_sending.py
+++ b/pyrit/executor/attack/multi_turn/multi_prompt_sending.py
@@ -47,7 +47,7 @@ class MultiPromptSendingAttackParameters(AttackParameters):
     Only accepts objective and user_messages fields.
     """
 
-    user_messages: Optional[list[Message]] = None
+    user_messages: list[Message] | None = None
 
     @classmethod
     async def from_seed_group_async(
@@ -137,9 +137,9 @@ def __init__(
         self,
         *,
         objective_target: PromptTarget = REQUIRED_VALUE,  # type: ignore[ty:invalid-parameter-default]
-        attack_converter_config: Optional[AttackConverterConfig] = None,
-        attack_scoring_config: Optional[AttackScoringConfig] = None,
-        prompt_normalizer: Optional[PromptNormalizer] = None,
+        attack_converter_config: AttackConverterConfig | None = None,
+        attack_scoring_config: AttackScoringConfig | None = None,
+        prompt_normalizer: PromptNormalizer | None = None,
     ) -> None:
         """
         Initialize the multi-prompt sending attack strategy.
@@ -179,7 +179,7 @@ def __init__(
             prompt_normalizer=self._prompt_normalizer,
         )
 
-    def get_attack_scoring_config(self) -> Optional[AttackScoringConfig]:
+    def get_attack_scoring_config(self) -> AttackScoringConfig | None:
         """
         Get the attack scoring configuration used by this strategy.
 
@@ -301,10 +301,10 @@ async def _perform_async(self, *, context: MultiTurnAttackContext[Any]) -> Attac
     def _determine_attack_outcome(
         self,
         *,
-        response: Optional[Message],
-        score: Optional[Score],
+        response: Message | None,
+        score: Score | None,
         context: MultiTurnAttackContext[Any],
-    ) -> tuple[AttackOutcome, Optional[str]]:
+    ) -> tuple[AttackOutcome, str | None]:
         """
         Determine the outcome of the attack based on the response and score.
 
@@ -340,7 +340,7 @@ async def _teardown_async(self, *, context: MultiTurnAttackContext[Any]) -> None
 
     async def _send_prompt_to_objective_target_async(
         self, *, current_message: Message, context: MultiTurnAttackContext[Any]
-    ) -> Optional[Message]:
+    ) -> Message | None:
         """
         Send the prompt to the target and return the response.
 
@@ -370,7 +370,7 @@ async def _send_prompt_to_objective_target_async(
                 attack_identifier=self.get_identifier(),
             )
 
-    async def _evaluate_response_async(self, *, response: Message, objective: str) -> Optional[Score]:
+    async def _evaluate_response_async(self, *, response: Message, objective: str) -> Score | None:
         """
         Evaluate the response against the objective using the configured scorers.
 
diff --git a/pyrit/executor/attack/multi_turn/multi_turn_attack_strategy.py b/pyrit/executor/attack/multi_turn/multi_turn_attack_strategy.py
index 809b150988..6416e9570d 100644
--- a/pyrit/executor/attack/multi_turn/multi_turn_attack_strategy.py
+++ b/pyrit/executor/attack/multi_turn/multi_turn_attack_strategy.py
@@ -7,7 +7,7 @@
 import uuid
 from abc import ABC
 from dataclasses import dataclass, field
-from typing import TYPE_CHECKING, Any, Optional, TypeVar
+from typing import TYPE_CHECKING, Any, TypeVar
 
 from pyrit.common.logger import logger
 from pyrit.executor.attack.core.attack_parameters import AttackParameters, AttackParamsT
@@ -58,10 +58,10 @@ class MultiTurnAttackContext(AttackContext[AttackParamsT]):
     executed_turns: int = 0
 
     # Model response produced in the latest turn
-    last_response: Optional[Message] = None
+    last_response: Message | None = None
 
     # Score assigned to the latest response by a scorer component
-    last_score: Optional[Score] = None
+    last_score: Score | None = None
 
 
 class MultiTurnAttackStrategy(AttackStrategy[MultiTurnAttackStrategyContextT, AttackStrategyResultT], ABC):
diff --git a/pyrit/executor/attack/multi_turn/red_teaming.py b/pyrit/executor/attack/multi_turn/red_teaming.py
index 84cb085fca..57c7a12f3b 100644
--- a/pyrit/executor/attack/multi_turn/red_teaming.py
+++ b/pyrit/executor/attack/multi_turn/red_teaming.py
@@ -6,7 +6,7 @@
 import enum
 import logging
 from pathlib import Path
-from typing import TYPE_CHECKING, Any, Optional, Union
+from typing import TYPE_CHECKING, Any
 
 from pyrit.common.apply_defaults import REQUIRED_VALUE, apply_defaults
 from pyrit.common.path import EXECUTOR_RED_TEAM_PATH
@@ -100,9 +100,9 @@ def __init__(
         *,
         objective_target: PromptTarget = REQUIRED_VALUE,  # type: ignore[ty:invalid-parameter-default]
         attack_adversarial_config: AttackAdversarialConfig,
-        attack_converter_config: Optional[AttackConverterConfig] = None,
-        attack_scoring_config: Optional[AttackScoringConfig] = None,
-        prompt_normalizer: Optional[PromptNormalizer] = None,
+        attack_converter_config: AttackConverterConfig | None = None,
+        attack_scoring_config: AttackScoringConfig | None = None,
+        prompt_normalizer: PromptNormalizer | None = None,
         max_turns: int = 10,
         score_last_turn_only: bool = False,
     ) -> None:
@@ -175,7 +175,7 @@ def __init__(
         self._max_turns = max_turns
         self._score_last_turn_only = score_last_turn_only
 
-    def get_attack_scoring_config(self) -> Optional[AttackScoringConfig]:
+    def get_attack_scoring_config(self) -> AttackScoringConfig | None:
         """
         Get the attack scoring configuration used by this strategy.
 
@@ -578,7 +578,7 @@ async def _send_prompt_to_objective_target_async(
 
         return response
 
-    async def _score_response_async(self, *, context: MultiTurnAttackContext[Any]) -> Optional[Score]:
+    async def _score_response_async(self, *, context: MultiTurnAttackContext[Any]) -> Score | None:
         """
         Evaluate the objective target's response with the objective scorer.
 
@@ -613,7 +613,7 @@ async def _score_response_async(self, *, context: MultiTurnAttackContext[Any]) -
         objective_scores = scoring_results
         return objective_scores[0] if objective_scores else None
 
-    def _set_adversarial_chat_seed_prompt(self, *, seed_prompt: Union[str, SeedPrompt]) -> None:
+    def _set_adversarial_chat_seed_prompt(self, *, seed_prompt: str | SeedPrompt) -> None:
         """
         Set the seed prompt for the adversarial chat.
 
diff --git a/pyrit/executor/attack/multi_turn/simulated_conversation.py b/pyrit/executor/attack/multi_turn/simulated_conversation.py
index a814424c92..895516243c 100644
--- a/pyrit/executor/attack/multi_turn/simulated_conversation.py
+++ b/pyrit/executor/attack/multi_turn/simulated_conversation.py
@@ -11,7 +11,7 @@
 from __future__ import annotations
 
 import logging
-from typing import TYPE_CHECKING, Optional, Union
+from typing import TYPE_CHECKING
 
 from pyrit.executor.attack.core.attack_config import (
     AttackAdversarialConfig,
@@ -39,11 +39,11 @@ async def generate_simulated_conversation_async(
     objective_scorer: TrueFalseScorer,
     num_turns: int = 3,
     starting_sequence: int = 0,
-    adversarial_chat_system_prompt_path: Union[str, Path],
-    simulated_target_system_prompt_path: Optional[Union[str, Path]] = None,
-    next_message_system_prompt_path: Optional[Union[str, Path]] = None,
-    attack_converter_config: Optional[AttackConverterConfig] = None,
-    memory_labels: Optional[dict[str, str]] = None,
+    adversarial_chat_system_prompt_path: str | Path,
+    simulated_target_system_prompt_path: str | Path | None = None,
+    next_message_system_prompt_path: str | Path | None = None,
+    attack_converter_config: AttackConverterConfig | None = None,
+    memory_labels: dict[str, str] | None = None,
 ) -> list[SeedPrompt]:
     """
     Generate a simulated conversation between an adversarial chat and a target.
@@ -171,7 +171,7 @@ async def _generate_next_message_async(
     objective: str,
     conversation_messages: list[Message],
     adversarial_chat: PromptTarget,
-    next_message_system_prompt_path: Union[str, Path],
+    next_message_system_prompt_path: str | Path,
 ) -> Message:
     """
     Generate a single next message using the adversarial chat LLM.
diff --git a/pyrit/executor/attack/multi_turn/tree_of_attacks.py b/pyrit/executor/attack/multi_turn/tree_of_attacks.py
index 94f3bc9ac1..543e48d470 100644
--- a/pyrit/executor/attack/multi_turn/tree_of_attacks.py
+++ b/pyrit/executor/attack/multi_turn/tree_of_attacks.py
@@ -106,8 +106,8 @@ def __init__(
         self,
         *,
         objective_scorer: FloatScaleThresholdScorer,
-        refusal_scorer: Optional[TrueFalseScorer] = None,
-        auxiliary_scorers: Optional[list[Scorer]] = None,
+        refusal_scorer: TrueFalseScorer | None = None,
+        auxiliary_scorers: list[Scorer] | None = None,
         use_score_as_feedback: bool = True,
     ) -> None:
         """
@@ -171,9 +171,9 @@ class TAPAttackContext(MultiTurnAttackContext[Any]):
     nodes: list["_TreeOfAttacksNode"] = field(default_factory=list)
 
     # Best conversation ID and score found during the attack
-    best_conversation_id: Optional[str] = None
-    best_objective_score: Optional[Score] = None
-    best_adversarial_conversation_id: Optional[str] = None
+    best_conversation_id: str | None = None
+    best_objective_score: Score | None = None
+    best_adversarial_conversation_id: str | None = None
 
 
 class TAPAttackResult(AttackResult):
@@ -185,7 +185,7 @@ class TAPAttackResult(AttackResult):
     """
 
     @property
-    def tree_visualization(self) -> Optional[Tree]:
+    def tree_visualization(self) -> Tree | None:
         """Get the tree visualization from metadata."""
         return self.metadata.get("tree_visualization", None)
 
@@ -235,12 +235,12 @@ def auxiliary_scores_summary(self, value: dict[str, float]) -> None:
         self.metadata["auxiliary_scores_summary"] = value
 
     @property
-    def best_adversarial_conversation_id(self) -> Optional[str]:
+    def best_adversarial_conversation_id(self) -> str | None:
         """Get the adversarial conversation ID for the best-scoring branch."""
-        return cast("Optional[str]", self.metadata.get("best_adversarial_conversation_id", None))
+        return cast("str | None", self.metadata.get("best_adversarial_conversation_id", None))
 
     @best_adversarial_conversation_id.setter
-    def best_adversarial_conversation_id(self, value: Optional[str]) -> None:
+    def best_adversarial_conversation_id(self, value: str | None) -> None:
         """Set the best adversarial conversation ID."""
         self.metadata["best_adversarial_conversation_id"] = value
 
@@ -285,16 +285,16 @@ def __init__(
         adversarial_chat_system_seed_prompt: SeedPrompt,
         desired_response_prefix: str,
         objective_scorer: Scorer,
-        on_topic_scorer: Optional[Scorer],
+        on_topic_scorer: Scorer | None,
         request_converters: list[PromptConverterConfiguration],
         response_converters: list[PromptConverterConfiguration],
-        auxiliary_scorers: Optional[list[Scorer]],
+        auxiliary_scorers: list[Scorer] | None,
         attack_id: ComponentIdentifier,
         attack_strategy_name: str,
-        memory_labels: Optional[dict[str, str]] = None,
-        parent_id: Optional[str] = None,
-        prompt_normalizer: Optional[PromptNormalizer] = None,
-        initial_prompt: Optional[Message] = None,
+        memory_labels: dict[str, str] | None = None,
+        parent_id: str | None = None,
+        prompt_normalizer: PromptNormalizer | None = None,
+        initial_prompt: Message | None = None,
     ) -> None:
         """
         Initialize a tree node.
@@ -353,21 +353,21 @@ def __init__(
         # Execution results (populated after send_prompt_async)
         self.completed = False
         self.off_topic = False
-        self.objective_score: Optional[Score] = None
+        self.objective_score: Score | None = None
         self.auxiliary_scores: dict[str, Score] = {}
-        self.last_prompt_sent: Optional[str] = None
-        self.last_response: Optional[str] = None
-        self.error_message: Optional[str] = None
+        self.last_prompt_sent: str | None = None
+        self.last_response: str | None = None
+        self.error_message: str | None = None
 
         # Context from prepended conversation (for adversarial chat system prompt)
-        self._conversation_context: Optional[str] = None
+        self._conversation_context: str | None = None
 
         # Initial prompt for first turn (bypasses adversarial chat generation)
         # This supports multimodal messages
-        self._initial_prompt: Optional[Message] = initial_prompt
+        self._initial_prompt: Message | None = initial_prompt
 
         # Current objective (set when send_prompt_async is called)
-        self._objective: Optional[str] = None
+        self._objective: str | None = None
 
     async def initialize_with_prepended_conversation_async(
         self,
@@ -1925,8 +1925,8 @@ def _create_attack_node(
         self,
         *,
         context: TAPAttackContext,
-        parent_id: Optional[str] = None,
-        initial_prompt: Optional[Message] = None,
+        parent_id: str | None = None,
+        initial_prompt: Message | None = None,
     ) -> _TreeOfAttacksNode:
         """
         Create a new attack node with the configured settings.
@@ -2037,7 +2037,7 @@ def _format_node_result(self, node: _TreeOfAttacksNode) -> str:
         unnormalized_score = round(1 + normalized_score * 9)
         return f"Score: {unnormalized_score}/10"
 
-    def _create_on_topic_scorer(self, objective: str) -> Optional[Scorer]:
+    def _create_on_topic_scorer(self, objective: str) -> Scorer | None:
         """
         Create an on-topic scorer if enabled, configured for the specific objective.
 
@@ -2187,7 +2187,7 @@ def _create_attack_result(
 
         return result
 
-    def _get_last_response_from_conversation(self, conversation_id: Optional[str]) -> Optional[MessagePiece]:
+    def _get_last_response_from_conversation(self, conversation_id: str | None) -> MessagePiece | None:
         """
         Retrieve the last response from a conversation.
 
@@ -2261,7 +2261,7 @@ async def execute_async(
         self,
         *,
         objective: str,
-        memory_labels: Optional[dict[str, str]] = None,
+        memory_labels: dict[str, str] | None = None,
         **kwargs: Any,
     ) -> TAPAttackResult: ...
 
diff --git a/pyrit/executor/attack/single_turn/context_compliance.py b/pyrit/executor/attack/single_turn/context_compliance.py
index 61e58b9e5f..05bc22621b 100644
--- a/pyrit/executor/attack/single_turn/context_compliance.py
+++ b/pyrit/executor/attack/single_turn/context_compliance.py
@@ -3,7 +3,7 @@
 
 import logging
 from pathlib import Path
-from typing import Any, Optional
+from typing import Any
 
 from pyrit.common.apply_defaults import REQUIRED_VALUE, apply_defaults
 from pyrit.common.path import EXECUTOR_SEED_PROMPT_PATH
@@ -59,12 +59,12 @@ def __init__(
         *,
         objective_target: PromptTarget = REQUIRED_VALUE,  # type: ignore[ty:invalid-parameter-default]
         attack_adversarial_config: AttackAdversarialConfig,
-        attack_converter_config: Optional[AttackConverterConfig] = None,
-        attack_scoring_config: Optional[AttackScoringConfig] = None,
-        prompt_normalizer: Optional[PromptNormalizer] = None,
+        attack_converter_config: AttackConverterConfig | None = None,
+        attack_scoring_config: AttackScoringConfig | None = None,
+        prompt_normalizer: PromptNormalizer | None = None,
         max_attempts_on_failure: int = 0,
-        context_description_instructions_path: Optional[Path] = None,
-        affirmative_response: Optional[str] = None,
+        context_description_instructions_path: Path | None = None,
+        affirmative_response: str | None = None,
     ) -> None:
         """
         Initialize the context compliance attack strategy.
diff --git a/pyrit/executor/attack/single_turn/flip_attack.py b/pyrit/executor/attack/single_turn/flip_attack.py
index 035ef2212d..878ff1da1a 100644
--- a/pyrit/executor/attack/single_turn/flip_attack.py
+++ b/pyrit/executor/attack/single_turn/flip_attack.py
@@ -4,7 +4,7 @@
 import logging
 import pathlib
 import uuid
-from typing import Any, Optional
+from typing import Any
 
 from pyrit.common.apply_defaults import REQUIRED_VALUE, apply_defaults
 from pyrit.common.path import EXECUTOR_SEED_PROMPT_PATH
@@ -41,9 +41,9 @@ def __init__(
         self,
         *,
         objective_target: PromptTarget = REQUIRED_VALUE,  # type: ignore[ty:invalid-parameter-default]
-        attack_converter_config: Optional[AttackConverterConfig] = None,
-        attack_scoring_config: Optional[AttackScoringConfig] = None,
-        prompt_normalizer: Optional[PromptNormalizer] = None,
+        attack_converter_config: AttackConverterConfig | None = None,
+        attack_scoring_config: AttackScoringConfig | None = None,
+        prompt_normalizer: PromptNormalizer | None = None,
         max_attempts_on_failure: int = 0,
     ) -> None:
         """
diff --git a/pyrit/executor/attack/single_turn/many_shot_jailbreak.py b/pyrit/executor/attack/single_turn/many_shot_jailbreak.py
index e4225b3ddb..6c9f81bbf4 100644
--- a/pyrit/executor/attack/single_turn/many_shot_jailbreak.py
+++ b/pyrit/executor/attack/single_turn/many_shot_jailbreak.py
@@ -3,7 +3,7 @@
 
 import json
 import logging
-from typing import Any, Optional
+from typing import Any
 
 from pyrit.common.apply_defaults import REQUIRED_VALUE, apply_defaults
 from pyrit.common.path import DATASETS_PATH, JAILBREAK_TEMPLATES_PATH
@@ -50,12 +50,12 @@ def __init__(
         self,
         *,
         objective_target: PromptTarget = REQUIRED_VALUE,  # type: ignore[ty:invalid-parameter-default]
-        attack_converter_config: Optional[AttackConverterConfig] = None,
-        attack_scoring_config: Optional[AttackScoringConfig] = None,
-        prompt_normalizer: Optional[PromptNormalizer] = None,
+        attack_converter_config: AttackConverterConfig | None = None,
+        attack_scoring_config: AttackScoringConfig | None = None,
+        prompt_normalizer: PromptNormalizer | None = None,
         max_attempts_on_failure: int = 0,
         example_count: int = 100,
-        many_shot_examples: Optional[list[dict[str, str]]] = None,
+        many_shot_examples: list[dict[str, str]] | None = None,
     ) -> None:
         """
         Args:
diff --git a/pyrit/executor/attack/single_turn/prompt_sending.py b/pyrit/executor/attack/single_turn/prompt_sending.py
index f3c8aeedae..8ca2b4dabe 100644
--- a/pyrit/executor/attack/single_turn/prompt_sending.py
+++ b/pyrit/executor/attack/single_turn/prompt_sending.py
@@ -3,7 +3,7 @@
 
 import logging
 import uuid
-from typing import Any, Optional
+from typing import Any
 
 from pyrit.common.apply_defaults import REQUIRED_VALUE, apply_defaults
 from pyrit.common.utils import warn_if_set
@@ -55,12 +55,12 @@ def __init__(
         self,
         *,
         objective_target: PromptTarget = REQUIRED_VALUE,  # type: ignore[ty:invalid-parameter-default]
-        attack_converter_config: Optional[AttackConverterConfig] = None,
-        attack_scoring_config: Optional[AttackScoringConfig] = None,
-        prompt_normalizer: Optional[PromptNormalizer] = None,
+        attack_converter_config: AttackConverterConfig | None = None,
+        attack_scoring_config: AttackScoringConfig | None = None,
+        prompt_normalizer: PromptNormalizer | None = None,
         max_attempts_on_failure: int = 0,
         params_type: type[AttackParamsT] = AttackParameters,  # type: ignore[ty:invalid-parameter-default]
-        prepended_conversation_config: Optional[PrependedConversationConfig] = None,
+        prepended_conversation_config: PrependedConversationConfig | None = None,
     ) -> None:
         """
         Initialize the prompt injection attack strategy.
@@ -119,7 +119,7 @@ def __init__(
         # Store the prepended conversation configuration
         self._prepended_conversation_config = prepended_conversation_config
 
-    def get_attack_scoring_config(self) -> Optional[AttackScoringConfig]:
+    def get_attack_scoring_config(self) -> AttackScoringConfig | None:
         """
         Get the attack scoring configuration used by this strategy.
 
@@ -242,8 +242,8 @@ async def _perform_async(self, *, context: SingleTurnAttackContext[Any]) -> Atta
         )
 
     def _determine_attack_outcome(
-        self, *, response: Optional[Message], score: Optional[Score], context: SingleTurnAttackContext[Any]
-    ) -> tuple[AttackOutcome, Optional[str]]:
+        self, *, response: Message | None, score: Score | None, context: SingleTurnAttackContext[Any]
+    ) -> tuple[AttackOutcome, str | None]:
         """
         Determine the outcome of the attack based on the response and score.
 
@@ -299,7 +299,7 @@ def _get_message(self, context: SingleTurnAttackContext[Any]) -> Message:
 
     async def _send_prompt_to_objective_target_async(
         self, *, message: Message, context: SingleTurnAttackContext[Any]
-    ) -> Optional[Message]:
+    ) -> Message | None:
         """
         Send the prompt to the target and return the response.
 
@@ -334,7 +334,7 @@ async def _evaluate_response_async(
         *,
         response: Message,
         objective: str,
-    ) -> Optional[Score]:
+    ) -> Score | None:
         """
         Evaluate the response against the objective using the configured scorers.
 
diff --git a/pyrit/executor/attack/single_turn/role_play.py b/pyrit/executor/attack/single_turn/role_play.py
index dfa21c8aa9..e061c496e3 100644
--- a/pyrit/executor/attack/single_turn/role_play.py
+++ b/pyrit/executor/attack/single_turn/role_play.py
@@ -4,7 +4,7 @@
 import enum
 import logging
 import pathlib
-from typing import Any, Optional
+from typing import Any
 
 from pyrit.common.apply_defaults import REQUIRED_VALUE, apply_defaults
 from pyrit.common.path import EXECUTOR_SEED_PROMPT_PATH
@@ -68,9 +68,9 @@ def __init__(
         objective_target: PromptTarget = REQUIRED_VALUE,  # type: ignore[ty:invalid-parameter-default]
         attack_adversarial_config: AttackAdversarialConfig,
         role_play_definition_path: pathlib.Path,
-        attack_converter_config: Optional[AttackConverterConfig] = None,
-        attack_scoring_config: Optional[AttackScoringConfig] = None,
-        prompt_normalizer: Optional[PromptNormalizer] = None,
+        attack_converter_config: AttackConverterConfig | None = None,
+        attack_scoring_config: AttackScoringConfig | None = None,
+        prompt_normalizer: PromptNormalizer | None = None,
         max_attempts_on_failure: int = 0,
     ) -> None:
         """
@@ -157,7 +157,7 @@ async def _rephrase_objective_async(self, *, objective: str) -> str:
         result = await converter.convert_async(prompt=objective, input_type="text")
         return result.output_text
 
-    async def _get_conversation_start_async(self) -> Optional[list[Message]]:
+    async def _get_conversation_start_async(self) -> list[Message] | None:
         """
         Get the role-play conversation start messages.
 
diff --git a/pyrit/executor/attack/single_turn/single_turn_attack_strategy.py b/pyrit/executor/attack/single_turn/single_turn_attack_strategy.py
index d719861646..c4c3dc8997 100644
--- a/pyrit/executor/attack/single_turn/single_turn_attack_strategy.py
+++ b/pyrit/executor/attack/single_turn/single_turn_attack_strategy.py
@@ -7,7 +7,7 @@
 import uuid
 from abc import ABC
 from dataclasses import dataclass, field
-from typing import TYPE_CHECKING, Any, Optional, Union
+from typing import TYPE_CHECKING, Any
 
 from pyrit.common.logger import logger
 from pyrit.executor.attack.core.attack_parameters import AttackParameters, AttackParamsT
@@ -32,10 +32,10 @@ class SingleTurnAttackContext(AttackContext[AttackParamsT]):
     conversation_id: str = field(default_factory=lambda: str(uuid.uuid4()))
 
     # System prompt for chat-based targets
-    system_prompt: Optional[str] = None
+    system_prompt: str | None = None
 
     # Arbitrary metadata that downstream attacks or scorers may attach
-    metadata: Optional[dict[str, Union[str, int]]] = None
+    metadata: dict[str, str | int] | None = None
 
 
 class SingleTurnAttackStrategy(AttackStrategy[SingleTurnAttackContext[Any], AttackResult], ABC):
diff --git a/pyrit/executor/attack/single_turn/skeleton_key.py b/pyrit/executor/attack/single_turn/skeleton_key.py
index 3761cb9cb2..40190f5c25 100644
--- a/pyrit/executor/attack/single_turn/skeleton_key.py
+++ b/pyrit/executor/attack/single_turn/skeleton_key.py
@@ -3,7 +3,7 @@
 
 import logging
 from pathlib import Path
-from typing import Any, Optional
+from typing import Any
 
 from pyrit.common.apply_defaults import REQUIRED_VALUE, apply_defaults
 from pyrit.common.path import EXECUTOR_SEED_PROMPT_PATH
@@ -54,10 +54,10 @@ def __init__(
         self,
         *,
         objective_target: PromptTarget = REQUIRED_VALUE,  # type: ignore[ty:invalid-parameter-default]
-        attack_converter_config: Optional[AttackConverterConfig] = None,
-        attack_scoring_config: Optional[AttackScoringConfig] = None,
-        prompt_normalizer: Optional[PromptNormalizer] = None,
-        skeleton_key_prompt: Optional[str] = None,
+        attack_converter_config: AttackConverterConfig | None = None,
+        attack_scoring_config: AttackScoringConfig | None = None,
+        prompt_normalizer: PromptNormalizer | None = None,
+        skeleton_key_prompt: str | None = None,
         max_attempts_on_failure: int = 0,
     ) -> None:
         """
@@ -85,7 +85,7 @@ def __init__(
         # Load skeleton key prompt
         self._skeleton_key_prompt = self._load_skeleton_key_prompt(skeleton_key_prompt)
 
-    def _load_skeleton_key_prompt(self, skeleton_key_prompt: Optional[str]) -> str:
+    def _load_skeleton_key_prompt(self, skeleton_key_prompt: str | None) -> str:
         """
         Load the skeleton key prompt from the provided string or default file.
 
@@ -135,7 +135,7 @@ async def _perform_async(self, *, context: SingleTurnAttackContext[Any]) -> Atta
 
         return result
 
-    async def _send_skeleton_key_prompt_async(self, *, context: SingleTurnAttackContext[Any]) -> Optional[Message]:
+    async def _send_skeleton_key_prompt_async(self, *, context: SingleTurnAttackContext[Any]) -> Message | None:
         """
         Send the skeleton key prompt to the target to prime it for the attack.
 
diff --git a/pyrit/executor/benchmark/fairness_bias.py b/pyrit/executor/benchmark/fairness_bias.py
index aa4f0da3b5..e29fba9127 100644
--- a/pyrit/executor/benchmark/fairness_bias.py
+++ b/pyrit/executor/benchmark/fairness_bias.py
@@ -6,7 +6,7 @@
 import uuid
 from collections import Counter
 from dataclasses import dataclass, field
-from typing import Any, Optional, cast, overload
+from typing import Any, cast, overload
 
 from pyrit.common.utils import get_kwarg_param
 from pyrit.executor.attack.core import (
@@ -45,7 +45,7 @@ class FairnessBiasBenchmarkContext(StrategyContext):
     num_experiments: int = 1
 
     # Custom objective (optional) - if not provided, default will be generated
-    objective: Optional[str] = None
+    objective: str | None = None
 
     # Prepended conversation for context
     prepended_conversation: list[Message] = field(default_factory=list)
@@ -56,7 +56,7 @@ class FairnessBiasBenchmarkContext(StrategyContext):
     # Generated fields for the benchmark run
     generated_objective: str = field(default_factory=str)
     generated_story_prompt: str = field(default_factory=str)
-    generated_message: Optional[Message] = None
+    generated_message: Message | None = None
     experiment_results: list[dict[str, str]] = field(default_factory=list)
 
 
@@ -90,9 +90,9 @@ def __init__(
         self,
         *,
         objective_target: PromptTarget,
-        attack_converter_config: Optional[AttackConverterConfig] = None,
-        attack_scoring_config: Optional[AttackScoringConfig] = None,
-        prompt_normalizer: Optional[PromptNormalizer] = None,
+        attack_converter_config: AttackConverterConfig | None = None,
+        attack_scoring_config: AttackScoringConfig | None = None,
+        prompt_normalizer: PromptNormalizer | None = None,
         max_attempts_on_failure: int = 0,
     ) -> None:
         """
@@ -274,7 +274,7 @@ def _format_story_prompt(self, *, subject: str, story_type: str) -> str:
             f"and use pronouns to refer to the {subject} later in the text."
         )
 
-    def _extract_name(self, response: str) -> Optional[str]:
+    def _extract_name(self, response: str) -> str | None:
         """
         Extract person names using spaCy NER (if available) or fallback to regex.
         spaCy provides much more robust name extraction than simple regex patterns.
@@ -306,7 +306,7 @@ def _extract_name(self, response: str) -> Optional[str]:
                     return str(name)
         return None
 
-    def _extract_name_with_regex(self, response: str) -> Optional[str]:
+    def _extract_name_with_regex(self, response: str) -> str | None:
         """
         Fallback regex-based name extraction (original implementation with improvements).
 
@@ -365,7 +365,7 @@ def get_experiment_summary(self, *, context: FairnessBiasBenchmarkContext) -> di
             ],
         }
 
-    def get_last_context(self) -> Optional[FairnessBiasBenchmarkContext]:
+    def get_last_context(self) -> FairnessBiasBenchmarkContext | None:
         """
         Get the context from the last execution.
 
@@ -373,7 +373,7 @@ def get_last_context(self) -> Optional[FairnessBiasBenchmarkContext]:
             Optional[FairnessBiasBenchmarkContext]: The context from the most recent execution,
                 or None if no execution has occurred
         """
-        return cast("Optional[FairnessBiasBenchmarkContext]", getattr(self, "_last_context", None))
+        return cast("FairnessBiasBenchmarkContext | None", getattr(self, "_last_context", None))
 
     async def _teardown_async(self, *, context: FairnessBiasBenchmarkContext) -> None:
         """
@@ -391,9 +391,9 @@ async def execute_async(
         subject: str,
         story_type: str,
         num_experiments: int = 1,
-        objective: Optional[str] = None,
-        prepended_conversation: Optional[list[Message]] = None,
-        memory_labels: Optional[dict[str, str]] = None,
+        objective: str | None = None,
+        prepended_conversation: list[Message] | None = None,
+        memory_labels: dict[str, str] | None = None,
         **kwargs: Any,
     ) -> AttackResult: ...
 
diff --git a/pyrit/executor/benchmark/question_answering.py b/pyrit/executor/benchmark/question_answering.py
index 8f2307eba9..1e84619abf 100644
--- a/pyrit/executor/benchmark/question_answering.py
+++ b/pyrit/executor/benchmark/question_answering.py
@@ -4,7 +4,7 @@
 import logging
 import textwrap
 from dataclasses import dataclass, field
-from typing import Any, Optional, overload
+from typing import Any, overload
 
 from pyrit.common.utils import get_kwarg_param
 from pyrit.executor.attack.core import (
@@ -45,7 +45,7 @@ class QuestionAnsweringBenchmarkContext(StrategyContext):
     # The generated question prompt for the benchmark
     generated_question_prompt: str = field(default_factory=str)
     # The generated message for the benchmark
-    generated_message: Optional[Message] = None
+    generated_message: Message | None = None
 
 
 class QuestionAnsweringBenchmark(Strategy[QuestionAnsweringBenchmarkContext, AttackResult]):
@@ -84,9 +84,9 @@ def __init__(
         self,
         *,
         objective_target: PromptTarget,
-        attack_converter_config: Optional[AttackConverterConfig] = None,
-        attack_scoring_config: Optional[AttackScoringConfig] = None,
-        prompt_normalizer: Optional[PromptNormalizer] = None,
+        attack_converter_config: AttackConverterConfig | None = None,
+        attack_scoring_config: AttackScoringConfig | None = None,
+        prompt_normalizer: PromptNormalizer | None = None,
         objective_format_string: str = _DEFAULT_OBJECTIVE_FORMAT,
         question_asking_format_string: str = _DEFAULT_QUESTION_FORMAT,
         options_format_string: str = _DEFAULT_OPTIONS_FORMAT,
@@ -259,8 +259,8 @@ async def execute_async(
         self,
         *,
         question_answering_entry: QuestionAnsweringEntry,
-        prepended_conversation: Optional[list[Message]] = None,
-        memory_labels: Optional[dict[str, str]] = None,
+        prepended_conversation: list[Message] | None = None,
+        memory_labels: dict[str, str] | None = None,
         **kwargs: Any,
     ) -> AttackResult: ...
 
diff --git a/pyrit/executor/core/strategy.py b/pyrit/executor/core/strategy.py
index 38a6c9261f..df10b0b0ca 100644
--- a/pyrit/executor/core/strategy.py
+++ b/pyrit/executor/core/strategy.py
@@ -12,7 +12,7 @@
 from copy import deepcopy
 from dataclasses import dataclass
 from enum import Enum
-from typing import TYPE_CHECKING, Any, Generic, Optional, TypeVar
+from typing import TYPE_CHECKING, Any, Generic, TypeVar
 
 from pyrit.common import default_values
 from pyrit.common.logger import logger
@@ -85,10 +85,10 @@ class StrategyEventData(Generic[StrategyContextT, StrategyResultT]):
 
     # Context and result of the strategy
     context: StrategyContextT
-    result: Optional[StrategyResultT] = None
+    result: StrategyResultT | None = None
 
     # Optional error if the event is related to an error
-    error: Optional[Exception] = None
+    error: Exception | None = None
 
 
 class StrategyEventHandler(ABC, Generic[StrategyContextT, StrategyResultT]):
@@ -157,7 +157,7 @@ def __init__(
         self,
         *,
         context_type: type[StrategyContextT],
-        event_handler: Optional[StrategyEventHandler[StrategyContextT, StrategyResultT]] = None,
+        event_handler: StrategyEventHandler[StrategyContextT, StrategyResultT] | None = None,
         logger: logging.Logger = logger,
     ) -> None:
         """
@@ -250,8 +250,8 @@ async def _handle_event_async(
         *,
         event: StrategyEvent,
         context: StrategyContextT,
-        result: Optional[StrategyResultT] = None,
-        error: Optional[Exception] = None,
+        result: StrategyResultT | None = None,
+        error: Exception | None = None,
     ) -> None:
         """
         Handle a strategy event by notifying all registered event handlers.
diff --git a/pyrit/executor/promptgen/anecdoctor.py b/pyrit/executor/promptgen/anecdoctor.py
index 3e32fa4faa..68cdf51785 100644
--- a/pyrit/executor/promptgen/anecdoctor.py
+++ b/pyrit/executor/promptgen/anecdoctor.py
@@ -7,7 +7,7 @@
 import uuid
 from dataclasses import dataclass, field
 from pathlib import Path
-from typing import TYPE_CHECKING, Any, Optional, Union, overload
+from typing import TYPE_CHECKING, Any, overload
 
 import yaml
 
@@ -103,9 +103,9 @@ def __init__(
         self,
         *,
         objective_target: PromptTarget,
-        processing_model: Optional[PromptTarget] = None,
-        converter_config: Optional[StrategyConverterConfig] = None,
-        prompt_normalizer: Optional[PromptNormalizer] = None,
+        processing_model: PromptTarget | None = None,
+        converter_config: StrategyConverterConfig | None = None,
+        prompt_normalizer: PromptNormalizer | None = None,
     ) -> None:
         """
         Initialize the Anecdoctor prompt generation strategy.
@@ -136,7 +136,7 @@ def __init__(
             self._system_prompt_template = self._load_prompt_from_yaml(yaml_filename=self._ANECDOCTOR_USE_KG_YAML)
             # Also preload the KG extraction prompt so `_extract_knowledge_graph_async` doesn't
             # repeat the file read + YAML parse on each invocation.
-            self._kg_prompt_template: Optional[str] = self._load_prompt_from_yaml(
+            self._kg_prompt_template: str | None = self._load_prompt_from_yaml(
                 yaml_filename=self._ANECDOCTOR_BUILD_KG_YAML
             )
         else:
@@ -146,8 +146,8 @@ def __init__(
     def _create_identifier(
         self,
         *,
-        params: Optional[dict[str, Any]] = None,
-        children: Optional[dict[str, Union[ComponentIdentifier, list[ComponentIdentifier]]]] = None,
+        params: dict[str, Any] | None = None,
+        children: dict[str, ComponentIdentifier | list[ComponentIdentifier]] | None = None,
     ) -> ComponentIdentifier:
         """
         Construct the identifier for this prompt generator.
@@ -160,7 +160,7 @@ def _create_identifier(
         Returns:
             ComponentIdentifier: The identifier for this prompt generator.
         """
-        all_children: dict[str, Union[ComponentIdentifier, list[ComponentIdentifier]]] = {
+        all_children: dict[str, ComponentIdentifier | list[ComponentIdentifier]] = {
             "objective_target": self._objective_target.get_identifier(),
         }
         if children:
@@ -286,7 +286,7 @@ async def _prepare_examples_async(self, *, context: AnecdoctorContext) -> str:
 
     async def _send_examples_to_target_async(
         self, *, formatted_examples: str, context: AnecdoctorContext
-    ) -> Optional[Message]:
+    ) -> Message | None:
         """
         Send the formatted examples to the target model.
 
@@ -414,7 +414,7 @@ async def execute_async(
         content_type: str,
         language: str,
         evaluation_data: list[str],
-        memory_labels: Optional[dict[str, str]] = None,
+        memory_labels: dict[str, str] | None = None,
         **kwargs: Any,
     ) -> AnecdoctorResult: ...
 
diff --git a/pyrit/executor/promptgen/core/prompt_generator_strategy.py b/pyrit/executor/promptgen/core/prompt_generator_strategy.py
index dc53003521..6db8d0bdd7 100644
--- a/pyrit/executor/promptgen/core/prompt_generator_strategy.py
+++ b/pyrit/executor/promptgen/core/prompt_generator_strategy.py
@@ -6,7 +6,7 @@
 import logging  # noqa: TC003
 from abc import ABC
 from dataclasses import dataclass
-from typing import Optional, TypeVar
+from typing import TypeVar
 
 from pyrit.common.logger import logger
 from pyrit.executor.core.strategy import (
@@ -70,9 +70,8 @@ def __init__(
         self,
         context_type: type[PromptGeneratorStrategyContextT],
         logger: logging.Logger = logger,
-        event_handler: Optional[
-            StrategyEventHandler[PromptGeneratorStrategyContextT, PromptGeneratorStrategyResultT]
-        ] = None,
+        event_handler: StrategyEventHandler[PromptGeneratorStrategyContextT, PromptGeneratorStrategyResultT]
+        | None = None,
     ) -> None:
         """
         Initialize the prompt generator strategy.
diff --git a/pyrit/executor/promptgen/fuzzer/fuzzer.py b/pyrit/executor/promptgen/fuzzer/fuzzer.py
index df04314069..adb596eb42 100644
--- a/pyrit/executor/promptgen/fuzzer/fuzzer.py
+++ b/pyrit/executor/promptgen/fuzzer/fuzzer.py
@@ -8,7 +8,7 @@
 import textwrap
 import uuid
 from dataclasses import dataclass, field
-from typing import TYPE_CHECKING, Any, Optional, Union, overload
+from typing import TYPE_CHECKING, Any, overload
 
 import numpy as np
 from colorama import Fore, Style
@@ -51,7 +51,7 @@ class _PromptNode:
     def __init__(
         self,
         template: str,
-        parent: Optional[_PromptNode] = None,
+        parent: _PromptNode | None = None,
     ) -> None:
         """
         Create the PromptNode instance.
@@ -66,7 +66,7 @@ def __init__(
         self.level: int = 0 if parent is None else parent.level + 1
         self.visited_num = 0
         self.rewards: float = 0
-        self.parent: Optional[_PromptNode] = None
+        self.parent: _PromptNode | None = None
         if parent is not None:
             self.add_parent(parent)
 
@@ -157,7 +157,7 @@ def _calculate_uct_score(self, *, node: _PromptNode, step: int) -> float:
         exploration = self.frequency_weight * np.sqrt(2 * np.log(step) / (node.visited_num + 0.01))
         return float(exploitation + exploration)
 
-    def update_rewards(self, path: list[_PromptNode], reward: float, last_node: Optional[_PromptNode] = None) -> None:
+    def update_rewards(self, path: list[_PromptNode], reward: float, last_node: _PromptNode | None = None) -> None:
         """
         Update rewards for nodes in the path.
 
@@ -185,19 +185,19 @@ class FuzzerContext(PromptGeneratorStrategyContext):
     # Per-execution input data
     prompts: list[str]
     prompt_templates: list[str]
-    max_query_limit: Optional[int] = None
+    max_query_limit: int | None = None
 
     # Tracking state
     total_target_query_count: int = 0
     total_jailbreak_count: int = 0
-    jailbreak_conversation_ids: list[Union[str, uuid.UUID]] = field(default_factory=list)
+    jailbreak_conversation_ids: list[str | uuid.UUID] = field(default_factory=list)
     executed_turns: int = 0
 
     # Tree structure
     initial_prompt_nodes: list[_PromptNode] = field(default_factory=list)
     new_prompt_nodes: list[_PromptNode] = field(default_factory=list)
     mcts_selected_path: list[_PromptNode] = field(default_factory=list)
-    last_choice_node: Optional[_PromptNode] = None
+    last_choice_node: _PromptNode | None = None
 
     # Optional memory labels to apply to the prompts
     memory_labels: dict[str, str] = field(default_factory=dict)
@@ -223,7 +223,7 @@ class FuzzerResult(PromptGeneratorStrategyResult):
 
     # Concrete fields instead of metadata storage
     successful_templates: list[str] = Field(default_factory=list)
-    jailbreak_conversation_ids: list[Union[str, uuid.UUID]] = Field(default_factory=list)
+    jailbreak_conversation_ids: list[str | uuid.UUID] = Field(default_factory=list)
     total_queries: int = 0
     templates_explored: int = 0
 
@@ -541,8 +541,8 @@ def with_default_scorer(
         objective_target: PromptTarget,
         template_converters: list[FuzzerConverter],
         scoring_target: PromptTarget,
-        converter_config: Optional[StrategyConverterConfig] = None,
-        prompt_normalizer: Optional[PromptNormalizer] = None,
+        converter_config: StrategyConverterConfig | None = None,
+        prompt_normalizer: PromptNormalizer | None = None,
         frequency_weight: float = _DEFAULT_FREQUENCY_WEIGHT,
         reward_penalty: float = _DEFAULT_REWARD_PENALTY,
         minimum_reward: float = _DEFAULT_MINIMUM_REWARD,
@@ -608,10 +608,10 @@ def __init__(
         *,
         objective_target: PromptTarget,
         template_converters: list[FuzzerConverter],
-        converter_config: Optional[StrategyConverterConfig] = None,
-        scorer: Optional[Scorer] = None,
+        converter_config: StrategyConverterConfig | None = None,
+        scorer: Scorer | None = None,
         scoring_success_threshold: float = 0.8,
-        prompt_normalizer: Optional[PromptNormalizer] = None,
+        prompt_normalizer: PromptNormalizer | None = None,
         frequency_weight: float = _DEFAULT_FREQUENCY_WEIGHT,
         reward_penalty: float = _DEFAULT_REWARD_PENALTY,
         minimum_reward: float = _DEFAULT_MINIMUM_REWARD,
@@ -685,8 +685,8 @@ def __init__(
     def _create_identifier(
         self,
         *,
-        params: Optional[dict[str, Any]] = None,
-        children: Optional[dict[str, Union[ComponentIdentifier, list[ComponentIdentifier]]]] = None,
+        params: dict[str, Any] | None = None,
+        children: dict[str, ComponentIdentifier | list[ComponentIdentifier]] | None = None,
     ) -> ComponentIdentifier:
         """
         Construct the identifier for this prompt generator.
@@ -699,7 +699,7 @@ def _create_identifier(
         Returns:
             ComponentIdentifier: The identifier for this prompt generator.
         """
-        all_children: dict[str, Union[ComponentIdentifier, list[ComponentIdentifier]]] = {
+        all_children: dict[str, ComponentIdentifier | list[ComponentIdentifier]] = {
             "objective_target": self._objective_target.get_identifier(),
         }
         if children:
@@ -1198,8 +1198,8 @@ async def execute_async(
         *,
         prompts: list[str],
         prompt_templates: list[str],
-        max_query_limit: Optional[int] = None,
-        memory_labels: Optional[dict[str, str]] = None,
+        max_query_limit: int | None = None,
+        memory_labels: dict[str, str] | None = None,
         **kwargs: Any,
     ) -> FuzzerResult: ...
 
diff --git a/pyrit/executor/promptgen/fuzzer/fuzzer_crossover_converter.py b/pyrit/executor/promptgen/fuzzer/fuzzer_crossover_converter.py
index 7e68a9907d..60ccbc1865 100644
--- a/pyrit/executor/promptgen/fuzzer/fuzzer_crossover_converter.py
+++ b/pyrit/executor/promptgen/fuzzer/fuzzer_crossover_converter.py
@@ -4,7 +4,7 @@
 import pathlib
 import random
 import uuid
-from typing import Any, Optional
+from typing import Any
 
 from pyrit.common.apply_defaults import apply_defaults
 from pyrit.common.path import CONVERTER_SEED_PROMPT_PATH
@@ -25,9 +25,9 @@ class FuzzerCrossOverConverter(FuzzerConverter):
     def __init__(
         self,
         *,
-        converter_target: Optional[PromptTarget] = None,
-        prompt_template: Optional[SeedPrompt] = None,
-        prompt_templates: Optional[list[str]] = None,
+        converter_target: PromptTarget | None = None,
+        prompt_template: SeedPrompt | None = None,
+        prompt_templates: list[str] | None = None,
     ) -> None:
         """
         Initialize the converter with the specified chat target and prompt templates.
diff --git a/pyrit/executor/promptgen/fuzzer/fuzzer_expand_converter.py b/pyrit/executor/promptgen/fuzzer/fuzzer_expand_converter.py
index 0c1f3fdf95..627ed159ed 100644
--- a/pyrit/executor/promptgen/fuzzer/fuzzer_expand_converter.py
+++ b/pyrit/executor/promptgen/fuzzer/fuzzer_expand_converter.py
@@ -3,7 +3,6 @@
 
 import pathlib
 import uuid
-from typing import Optional
 
 from pyrit.common.apply_defaults import apply_defaults
 from pyrit.common.path import CONVERTER_SEED_PROMPT_PATH
@@ -24,8 +23,8 @@ class FuzzerExpandConverter(FuzzerConverter):
     def __init__(
         self,
         *,
-        converter_target: Optional[PromptTarget] = None,
-        prompt_template: Optional[SeedPrompt] = None,
+        converter_target: PromptTarget | None = None,
+        prompt_template: SeedPrompt | None = None,
     ) -> None:
         """Initialize the expand converter with optional chat target and prompt template."""
         prompt_template = (
diff --git a/pyrit/executor/promptgen/fuzzer/fuzzer_rephrase_converter.py b/pyrit/executor/promptgen/fuzzer/fuzzer_rephrase_converter.py
index 10acff3fb6..d1f6783fc3 100644
--- a/pyrit/executor/promptgen/fuzzer/fuzzer_rephrase_converter.py
+++ b/pyrit/executor/promptgen/fuzzer/fuzzer_rephrase_converter.py
@@ -2,7 +2,6 @@
 # Licensed under the MIT license.
 
 import pathlib
-from typing import Optional
 
 from pyrit.common.apply_defaults import apply_defaults
 from pyrit.common.path import CONVERTER_SEED_PROMPT_PATH
@@ -20,7 +19,7 @@ class FuzzerRephraseConverter(FuzzerConverter):
 
     @apply_defaults
     def __init__(
-        self, *, converter_target: Optional[PromptTarget] = None, prompt_template: Optional[SeedPrompt] = None
+        self, *, converter_target: PromptTarget | None = None, prompt_template: SeedPrompt | None = None
     ) -> None:
         """Initialize the rephrase converter with optional chat target and prompt template."""
         prompt_template = (
diff --git a/pyrit/executor/promptgen/fuzzer/fuzzer_shorten_converter.py b/pyrit/executor/promptgen/fuzzer/fuzzer_shorten_converter.py
index 6258a5e7b3..dcc098f67c 100644
--- a/pyrit/executor/promptgen/fuzzer/fuzzer_shorten_converter.py
+++ b/pyrit/executor/promptgen/fuzzer/fuzzer_shorten_converter.py
@@ -2,7 +2,6 @@
 # Licensed under the MIT license.
 
 import pathlib
-from typing import Optional
 
 from pyrit.common.apply_defaults import apply_defaults
 from pyrit.common.path import CONVERTER_SEED_PROMPT_PATH
@@ -20,7 +19,7 @@ class FuzzerShortenConverter(FuzzerConverter):
 
     @apply_defaults
     def __init__(
-        self, *, converter_target: Optional[PromptTarget] = None, prompt_template: Optional[SeedPrompt] = None
+        self, *, converter_target: PromptTarget | None = None, prompt_template: SeedPrompt | None = None
     ) -> None:
         """Initialize the shorten converter with optional chat target and prompt template."""
         prompt_template = (
diff --git a/pyrit/executor/promptgen/fuzzer/fuzzer_similar_converter.py b/pyrit/executor/promptgen/fuzzer/fuzzer_similar_converter.py
index d7f2796579..25ec6fd2fb 100644
--- a/pyrit/executor/promptgen/fuzzer/fuzzer_similar_converter.py
+++ b/pyrit/executor/promptgen/fuzzer/fuzzer_similar_converter.py
@@ -2,7 +2,6 @@
 # Licensed under the MIT license.
 
 import pathlib
-from typing import Optional
 
 from pyrit.common.apply_defaults import apply_defaults
 from pyrit.common.path import CONVERTER_SEED_PROMPT_PATH
@@ -20,7 +19,7 @@ class FuzzerSimilarConverter(FuzzerConverter):
 
     @apply_defaults
     def __init__(
-        self, *, converter_target: Optional[PromptTarget] = None, prompt_template: Optional[SeedPrompt] = None
+        self, *, converter_target: PromptTarget | None = None, prompt_template: SeedPrompt | None = None
     ) -> None:
         """Initialize the similar converter with optional chat target and prompt template."""
         prompt_template = (
diff --git a/pyrit/executor/workflow/core/workflow_strategy.py b/pyrit/executor/workflow/core/workflow_strategy.py
index ba5a4a3369..179645b879 100644
--- a/pyrit/executor/workflow/core/workflow_strategy.py
+++ b/pyrit/executor/workflow/core/workflow_strategy.py
@@ -6,7 +6,7 @@
 import logging  # noqa: TC003
 from abc import ABC
 from dataclasses import dataclass
-from typing import Optional, TypeVar
+from typing import TypeVar
 
 from pyrit.common.logger import logger
 from pyrit.executor.core.strategy import (
@@ -109,7 +109,7 @@ def __init__(
         *,
         context_type: type[WorkflowContextT],
         logger: logging.Logger = logger,
-        event_handler: Optional[StrategyEventHandler[WorkflowContextT, WorkflowResultT]] = None,
+        event_handler: StrategyEventHandler[WorkflowContextT, WorkflowResultT] | None = None,
     ) -> None:
         """
         Initialize the workflow strategy with a specific context type and logger.
diff --git a/pyrit/executor/workflow/xpia.py b/pyrit/executor/workflow/xpia.py
index e981c46b63..426ad74cdb 100644
--- a/pyrit/executor/workflow/xpia.py
+++ b/pyrit/executor/workflow/xpia.py
@@ -5,7 +5,7 @@
 import uuid
 from dataclasses import dataclass, field
 from enum import Enum
-from typing import Any, Optional, Protocol, Union, overload
+from typing import Any, Protocol, overload
 
 from pyrit.common.utils import combine_dict, get_kwarg_param
 from pyrit.executor.core import StrategyConverterConfig
@@ -66,7 +66,7 @@ class XPIAContext(WorkflowContext):
     attack_content: Message
 
     # Callback to execute after the attack prompt is positioned in the attack location
-    processing_callback: Optional[XPIAProcessingCallback] = None
+    processing_callback: XPIAProcessingCallback | None = None
 
     # Conversation ID for the attack setup target
     attack_setup_target_conversation_id: str = field(default_factory=lambda: str(uuid.uuid4()))
@@ -75,7 +75,7 @@ class XPIAContext(WorkflowContext):
     processing_conversation_id: str = field(default_factory=lambda: str(uuid.uuid4()))
 
     # The prompt to send to the processing target (for test workflow)
-    processing_prompt: Optional[Message] = None
+    processing_prompt: Message | None = None
 
     # Additional labels that can be applied throughout the workflow
     memory_labels: dict[str, str] = field(default_factory=dict)
@@ -96,10 +96,10 @@ class XPIAResult(WorkflowResult):
     processing_response: str
 
     # Score if a scorer was used, None otherwise
-    score: Optional[Score] = None
+    score: Score | None = None
 
     # Response from the attack setup target
-    attack_setup_response: Optional[str] = None
+    attack_setup_response: str | None = None
 
     @property
     def success(self) -> bool:
@@ -145,9 +145,9 @@ def __init__(
         self,
         *,
         attack_setup_target: PromptTarget,
-        scorer: Optional[Scorer] = None,
-        converter_config: Optional[StrategyConverterConfig] = None,
-        prompt_normalizer: Optional[PromptNormalizer] = None,
+        scorer: Scorer | None = None,
+        converter_config: StrategyConverterConfig | None = None,
+        prompt_normalizer: PromptNormalizer | None = None,
         logger: logging.Logger = logger,
     ) -> None:
         """
@@ -178,8 +178,8 @@ def __init__(
     def _create_identifier(
         self,
         *,
-        params: Optional[dict[str, Any]] = None,
-        children: Optional[dict[str, Union[ComponentIdentifier, list[ComponentIdentifier]]]] = None,
+        params: dict[str, Any] | None = None,
+        children: dict[str, ComponentIdentifier | list[ComponentIdentifier]] | None = None,
     ) -> ComponentIdentifier:
         """
         Construct the identifier for this XPIA workflow.
@@ -192,7 +192,7 @@ def _create_identifier(
         Returns:
             ComponentIdentifier: The identifier for this XPIA workflow.
         """
-        all_children: dict[str, Union[ComponentIdentifier, list[ComponentIdentifier]]] = {
+        all_children: dict[str, ComponentIdentifier | list[ComponentIdentifier]] = {
             "attack_setup_target": self._attack_setup_target.get_identifier(),
         }
         if self._scorer:
@@ -382,7 +382,7 @@ async def _execute_processing_async(self, *, context: XPIAContext) -> str:
         self._logger.info(f'Received the following response from the processing target "{processing_response}"')
         return processing_response
 
-    async def _score_response_async(self, *, processing_response: str) -> Optional[Score]:
+    async def _score_response_async(self, *, processing_response: str) -> Score | None:
         """
         Score the processing response if a scorer is provided.
 
@@ -429,9 +429,9 @@ async def execute_async(
         self,
         *,
         attack_content: Message,
-        processing_callback: Optional[XPIAProcessingCallback] = None,
-        processing_prompt: Optional[Message] = None,
-        memory_labels: Optional[dict[str, str]] = None,
+        processing_callback: XPIAProcessingCallback | None = None,
+        processing_prompt: Message | None = None,
+        memory_labels: dict[str, str] | None = None,
         **kwargs: Any,
     ) -> XPIAResult: ...
 
@@ -503,8 +503,8 @@ def __init__(
         attack_setup_target: PromptTarget,
         processing_target: PromptTarget,
         scorer: Scorer,
-        converter_config: Optional[StrategyConverterConfig] = None,
-        prompt_normalizer: Optional[PromptNormalizer] = None,
+        converter_config: StrategyConverterConfig | None = None,
+        prompt_normalizer: PromptNormalizer | None = None,
         logger: logging.Logger = logger,
     ) -> None:
         """
@@ -605,8 +605,8 @@ def __init__(
         *,
         attack_setup_target: PromptTarget,
         scorer: Scorer,
-        converter_config: Optional[StrategyConverterConfig] = None,
-        prompt_normalizer: Optional[PromptNormalizer] = None,
+        converter_config: StrategyConverterConfig | None = None,
+        prompt_normalizer: PromptNormalizer | None = None,
         logger: logging.Logger = logger,
     ) -> None:
         """
diff --git a/pyrit/memory/azure_sql_memory.py b/pyrit/memory/azure_sql_memory.py
index 6723ae2842..0940fa8d82 100644
--- a/pyrit/memory/azure_sql_memory.py
+++ b/pyrit/memory/azure_sql_memory.py
@@ -7,7 +7,7 @@
 from collections.abc import MutableSequence, Sequence
 from contextlib import closing, suppress
 from datetime import datetime, timedelta, timezone
-from typing import TYPE_CHECKING, Any, Literal, Optional, TypeVar, Union, cast
+from typing import TYPE_CHECKING, Any, Literal, TypeVar, cast
 
 from sqlalchemy import and_, create_engine, event, exists, or_, text
 from sqlalchemy.engine.base import Engine
@@ -64,9 +64,9 @@ class AzureSQLMemory(MemoryInterface, metaclass=Singleton):
     def __init__(
         self,
         *,
-        connection_string: Optional[str] = None,
-        results_container_url: Optional[str] = None,
-        results_sas_token: Optional[str] = None,
+        connection_string: str | None = None,
+        results_container_url: str | None = None,
+        results_sas_token: str | None = None,
         verbose: bool = False,
         skip_schema_migration: bool = False,
         silent: bool = False,
@@ -93,12 +93,12 @@ def __init__(
             env_var_name=self.AZURE_STORAGE_ACCOUNT_DB_DATA_CONTAINER_URL, passed_value=results_container_url
         )
 
-        self._results_container_sas_token: Optional[str] = self._resolve_sas_token(
+        self._results_container_sas_token: str | None = self._resolve_sas_token(
             self.AZURE_STORAGE_ACCOUNT_DB_DATA_SAS_TOKEN, results_sas_token
         )
 
-        self._auth_token: Optional[AccessToken] = None
-        self._auth_token_expiry: Optional[int] = None
+        self._auth_token: AccessToken | None = None
+        self._auth_token_expiry: int | None = None
 
         self.results_path = self._results_container_url
 
@@ -116,7 +116,7 @@ def __init__(
         super().__init__()
 
     @staticmethod
-    def _resolve_sas_token(env_var_name: str, passed_value: Optional[str] = None) -> Optional[str]:
+    def _resolve_sas_token(env_var_name: str, passed_value: str | None = None) -> str | None:
         """
         Resolve the SAS token value, allowing a fallback to None for delegation SAS.
 
@@ -285,7 +285,7 @@ def _get_message_pieces_memory_label_conditions(self, *, memory_labels: dict[str
 
         return [or_(pme_match, are_match)]
 
-    def _get_metadata_conditions(self, *, prompt_metadata: dict[str, Union[str, int]]) -> list[TextClause]:
+    def _get_metadata_conditions(self, *, prompt_metadata: dict[str, str | int]) -> list[TextClause]:
         """
         Generate SQL conditions for filtering by prompt metadata.
 
@@ -310,7 +310,7 @@ def _get_metadata_conditions(self, *, prompt_metadata: dict[str, Union[str, int]
         return [condition]
 
     def _get_message_pieces_prompt_metadata_conditions(
-        self, *, prompt_metadata: dict[str, Union[str, int]]
+        self, *, prompt_metadata: dict[str, str | int]
     ) -> list[TextClause]:
         """
         Generate SQL conditions for filtering message pieces by prompt metadata.
@@ -325,7 +325,7 @@ def _get_message_pieces_prompt_metadata_conditions(
         """
         return self._get_metadata_conditions(prompt_metadata=prompt_metadata)
 
-    def _get_seed_metadata_conditions(self, *, metadata: dict[str, Union[str, int]]) -> TextClause:
+    def _get_seed_metadata_conditions(self, *, metadata: dict[str, str | int]) -> TextClause:
         """
         Generate SQL condition for filtering seed prompts by metadata.
 
@@ -800,10 +800,10 @@ def _query_entries(
         self,
         model_class: type[Model],
         *,
-        conditions: Optional[Any] = None,
+        conditions: Any | None = None,
         distinct: bool = False,
         join_scores: bool = False,
-        order_by: Optional[Any] = None,
+        order_by: Any | None = None,
         limit: int | None = None,
     ) -> MutableSequence[Model]:
         """
diff --git a/pyrit/memory/memory_embedding.py b/pyrit/memory/memory_embedding.py
index e2ddc26e77..3fc6592783 100644
--- a/pyrit/memory/memory_embedding.py
+++ b/pyrit/memory/memory_embedding.py
@@ -1,7 +1,6 @@
 # Copyright (c) Microsoft Corporation.
 # Licensed under the MIT license.
 
-from typing import Optional
 
 from pyrit.embedding import OpenAITextEmbedding
 from pyrit.memory.memory_models import EmbeddingDataEntry
@@ -16,7 +15,7 @@ class MemoryEmbedding:
         embedding_model (EmbeddingSupport): An instance of a class that supports embedding generation.
     """
 
-    def __init__(self, *, embedding_model: Optional[EmbeddingSupport] = None) -> None:
+    def __init__(self, *, embedding_model: EmbeddingSupport | None = None) -> None:
         """
         Initialize the memory embedding helper with a backing embedding model.
 
@@ -55,7 +54,7 @@ def generate_embedding_memory_data(self, *, message_piece: MessagePiece) -> Embe
         raise ValueError("Only text data is supported for embedding.")
 
 
-def default_memory_embedding_factory(embedding_model: Optional[EmbeddingSupport] = None) -> MemoryEmbedding | None:
+def default_memory_embedding_factory(embedding_model: EmbeddingSupport | None = None) -> MemoryEmbedding | None:
     """
     Create a MemoryEmbedding instance with default or provided embedding model.
 
diff --git a/pyrit/memory/memory_exporter.py b/pyrit/memory/memory_exporter.py
index 54e61505b3..b2a06668e7 100644
--- a/pyrit/memory/memory_exporter.py
+++ b/pyrit/memory/memory_exporter.py
@@ -4,7 +4,6 @@
 import csv
 import json
 from pathlib import Path
-from typing import Optional
 
 from pyrit.models import MessagePiece
 
@@ -30,7 +29,7 @@ def __init__(self) -> None:
         }
 
     def export_data(
-        self, data: list[MessagePiece], *, file_path: Optional[Path] = None, export_type: str = "json"
+        self, data: list[MessagePiece], *, file_path: Path | None = None, export_type: str = "json"
     ) -> None:
         """
         Export the provided data to a file in the specified format.
@@ -52,7 +51,7 @@ def export_data(
         else:
             raise ValueError(f"Unsupported export format: {export_type}")
 
-    def export_to_json(self, data: list[MessagePiece], file_path: Optional[Path] = None) -> None:
+    def export_to_json(self, data: list[MessagePiece], file_path: Path | None = None) -> None:
         """
         Export the provided data to a JSON file at the specified file path.
         Each item in the data list, representing a row from the table,
@@ -73,7 +72,7 @@ def export_to_json(self, data: list[MessagePiece], file_path: Optional[Path] = N
         with open(file_path, "w") as f:
             json.dump(export_data, f, indent=4)
 
-    def export_to_csv(self, data: list[MessagePiece], file_path: Optional[Path] = None) -> None:
+    def export_to_csv(self, data: list[MessagePiece], file_path: Path | None = None) -> None:
         """
         Export the provided data to a CSV file at the specified file path.
         Each item in the data list, representing a row from the table,
@@ -97,7 +96,7 @@ def export_to_csv(self, data: list[MessagePiece], file_path: Optional[Path] = No
             writer.writeheader()
             writer.writerows(export_data)
 
-    def export_to_markdown(self, data: list[MessagePiece], file_path: Optional[Path] = None) -> None:
+    def export_to_markdown(self, data: list[MessagePiece], file_path: Path | None = None) -> None:
         """
         Export the provided data to a Markdown file at the specified file path.
         Each item in the data list is converted to a dictionary and formatted as a table.
diff --git a/pyrit/memory/memory_interface.py b/pyrit/memory/memory_interface.py
index 26448f5b6c..9aeef709b5 100644
--- a/pyrit/memory/memory_interface.py
+++ b/pyrit/memory/memory_interface.py
@@ -11,7 +11,7 @@
 from contextlib import closing
 from datetime import datetime, timezone
 from pathlib import Path
-from typing import TYPE_CHECKING, Any, Literal, Optional, TypeVar, Union
+from typing import TYPE_CHECKING, Any, Literal, TypeVar
 
 from sqlalchemy import MetaData, and_, not_, or_
 from sqlalchemy.engine.base import Engine
@@ -93,7 +93,7 @@ def _uid() -> str:
         """Return a short unique suffix for bind-param deduplication."""
         return uuid.uuid4().hex[:8]
 
-    def __init__(self, embedding_model: Optional[Any] = None) -> None:
+    def __init__(self, embedding_model: Any | None = None) -> None:
         """
         Initialize the MemoryInterface.
 
@@ -110,7 +110,7 @@ def __init__(self, embedding_model: Optional[Any] = None) -> None:
         # Ensure cleanup at process exit
         self.cleanup()
 
-    def enable_embedding(self, embedding_model: Optional[Any] = None) -> None:
+    def enable_embedding(self, embedding_model: Any | None = None) -> None:
         """
         Enable embedding functionality for the memory interface.
 
@@ -318,9 +318,7 @@ def _get_message_pieces_memory_label_conditions(self, *, memory_labels: dict[str
         """
 
     @abc.abstractmethod
-    def _get_message_pieces_prompt_metadata_conditions(
-        self, *, prompt_metadata: dict[str, Union[str, int]]
-    ) -> list[Any]:
+    def _get_message_pieces_prompt_metadata_conditions(self, *, prompt_metadata: dict[str, str | int]) -> list[Any]:
         """
         Return a list of conditions for filtering memory entries based on prompt metadata.
 
@@ -333,7 +331,7 @@ def _get_message_pieces_prompt_metadata_conditions(
         """
 
     @abc.abstractmethod
-    def _get_seed_metadata_conditions(self, *, metadata: dict[str, Union[str, int]]) -> Any:
+    def _get_seed_metadata_conditions(self, *, metadata: dict[str, str | int]) -> Any:
         """
         Return a condition for filtering seed prompt entries based on prompt metadata.
 
@@ -362,10 +360,10 @@ def _query_entries(
         self,
         model_class: type[Model],
         *,
-        conditions: Optional[Any] = None,
+        conditions: Any | None = None,
         distinct: bool = False,
         join_scores: bool = False,
-        order_by: Optional[Any] = None,
+        order_by: Any | None = None,
         limit: int | None = None,
     ) -> MutableSequence[Model]:
         """
@@ -393,7 +391,7 @@ def _execute_batched_query(
         distinct: bool = False,
         join_scores: bool = False,
         batch_size: int | None = None,
-        order_by: Optional[Any] = None,
+        order_by: Any | None = None,
         limit: int | None = None,
     ) -> MutableSequence[Model]:
         """
@@ -708,12 +706,12 @@ def add_scores_to_memory(self, *, scores: Sequence[Score]) -> None:
     def get_scores(
         self,
         *,
-        score_ids: Optional[Sequence[str]] = None,
-        score_type: Optional[str] = None,
-        score_category: Optional[str] = None,
-        sent_after: Optional[datetime] = None,
-        sent_before: Optional[datetime] = None,
-        identifier_filters: Optional[Sequence[IdentifierFilter]] = None,
+        score_ids: Sequence[str] | None = None,
+        score_type: str | None = None,
+        score_category: str | None = None,
+        sent_after: datetime | None = None,
+        sent_before: datetime | None = None,
+        identifier_filters: Sequence[IdentifierFilter] | None = None,
     ) -> Sequence[Score]:
         """
         Retrieve a list of Score objects based on the specified filters.
@@ -772,19 +770,19 @@ def get_scores(
     def get_prompt_scores(
         self,
         *,
-        attack_id: Optional[str | uuid.UUID] = None,
-        role: Optional[str] = None,
-        conversation_id: Optional[str | uuid.UUID] = None,
-        prompt_ids: Optional[Sequence[str | uuid.UUID]] = None,
-        labels: Optional[dict[str, str]] = None,
-        prompt_metadata: Optional[dict[str, Union[str, int]]] = None,
-        sent_after: Optional[datetime] = None,
-        sent_before: Optional[datetime] = None,
-        original_values: Optional[Sequence[str]] = None,
-        converted_values: Optional[Sequence[str]] = None,
-        data_type: Optional[str] = None,
-        not_data_type: Optional[str] = None,
-        converted_value_sha256: Optional[Sequence[str]] = None,
+        attack_id: str | uuid.UUID | None = None,
+        role: str | None = None,
+        conversation_id: str | uuid.UUID | None = None,
+        prompt_ids: Sequence[str | uuid.UUID] | None = None,
+        labels: dict[str, str] | None = None,
+        prompt_metadata: dict[str, str | int] | None = None,
+        sent_after: datetime | None = None,
+        sent_before: datetime | None = None,
+        original_values: Sequence[str] | None = None,
+        converted_values: Sequence[str] | None = None,
+        data_type: str | None = None,
+        not_data_type: str | None = None,
+        converted_value_sha256: Sequence[str] | None = None,
     ) -> Sequence[Score]:
         """
         Retrieve scores attached to message pieces based on the specified filters.
@@ -879,20 +877,20 @@ def get_request_from_response(self, *, response: Message) -> Message:
     def get_message_pieces(
         self,
         *,
-        attack_id: Optional[str | uuid.UUID] = None,
-        role: Optional[str] = None,
-        conversation_id: Optional[str | uuid.UUID] = None,
-        prompt_ids: Optional[Sequence[str | uuid.UUID]] = None,
-        labels: Optional[dict[str, str]] = None,
-        prompt_metadata: Optional[dict[str, Union[str, int]]] = None,
-        sent_after: Optional[datetime] = None,
-        sent_before: Optional[datetime] = None,
-        original_values: Optional[Sequence[str]] = None,
-        converted_values: Optional[Sequence[str]] = None,
-        data_type: Optional[str] = None,
-        not_data_type: Optional[str] = None,
-        converted_value_sha256: Optional[Sequence[str]] = None,
-        identifier_filters: Optional[Sequence[IdentifierFilter]] = None,
+        attack_id: str | uuid.UUID | None = None,
+        role: str | None = None,
+        conversation_id: str | uuid.UUID | None = None,
+        prompt_ids: Sequence[str | uuid.UUID] | None = None,
+        labels: dict[str, str] | None = None,
+        prompt_metadata: dict[str, str | int] | None = None,
+        sent_after: datetime | None = None,
+        sent_before: datetime | None = None,
+        original_values: Sequence[str] | None = None,
+        converted_values: Sequence[str] | None = None,
+        data_type: str | None = None,
+        not_data_type: str | None = None,
+        converted_value_sha256: Sequence[str] | None = None,
+        identifier_filters: Sequence[IdentifierFilter] | None = None,
     ) -> Sequence[MessagePiece]:
         """
         Retrieve a list of MessagePiece objects based on the specified filters.
@@ -1164,7 +1162,7 @@ def update_labels_by_conversation_id(self, *, conversation_id: str, labels: dict
         )
 
     def update_prompt_metadata_by_conversation_id(
-        self, *, conversation_id: str, prompt_metadata: dict[str, Union[str, int]]
+        self, *, conversation_id: str, prompt_metadata: dict[str, str | int]
     ) -> bool:
         """
         Update the metadata of prompt entries in memory for a given conversation ID.
@@ -1232,20 +1230,20 @@ def cleanup(self) -> None:
     def get_seeds(
         self,
         *,
-        value: Optional[str] = None,
-        value_sha256: Optional[Sequence[str]] = None,
-        dataset_name: Optional[str] = None,
-        dataset_name_pattern: Optional[str] = None,
-        data_types: Optional[Sequence[str]] = None,
-        harm_categories: Optional[Sequence[str]] = None,
-        added_by: Optional[str] = None,
-        authors: Optional[Sequence[str]] = None,
-        groups: Optional[Sequence[str]] = None,
-        source: Optional[str] = None,
-        seed_type: Optional[SeedType] = None,
-        parameters: Optional[Sequence[str]] = None,
-        metadata: Optional[dict[str, Union[str, int]]] = None,
-        prompt_group_ids: Optional[Sequence[uuid.UUID]] = None,
+        value: str | None = None,
+        value_sha256: Sequence[str] | None = None,
+        dataset_name: str | None = None,
+        dataset_name_pattern: str | None = None,
+        data_types: Sequence[str] | None = None,
+        harm_categories: Sequence[str] | None = None,
+        added_by: str | None = None,
+        authors: Sequence[str] | None = None,
+        groups: Sequence[str] | None = None,
+        source: str | None = None,
+        seed_type: SeedType | None = None,
+        parameters: Sequence[str] | None = None,
+        metadata: dict[str, str | int] | None = None,
+        prompt_group_ids: Sequence[uuid.UUID] | None = None,
     ) -> Sequence[Seed]:
         """
         Retrieve a list of seed prompts based on the specified filters.
@@ -1327,7 +1325,7 @@ def get_seeds(
             raise
 
     def _add_list_conditions(
-        self, field: InstrumentedAttribute[Any], conditions: list[Any], values: Optional[Sequence[str]] = None
+        self, field: InstrumentedAttribute[Any], conditions: list[Any], values: Sequence[str] | None = None
     ) -> None:
         if values:
             conditions.extend(field.contains(value) for value in values)
@@ -1364,7 +1362,7 @@ async def _serialize_seed_value_async(self, prompt: Seed) -> str:
             serialized_prompt_value = str(serializer.value)
         return serialized_prompt_value or ""
 
-    async def add_seeds_to_memory_async(self, *, seeds: Sequence[Seed], added_by: Optional[str] = None) -> None:
+    async def add_seeds_to_memory_async(self, *, seeds: Sequence[Seed], added_by: str | None = None) -> None:
         """
         Insert a list of seeds into the memory storage.
 
@@ -1441,7 +1439,7 @@ def get_seed_dataset_names(self) -> Sequence[str]:
             raise
 
     async def add_seed_groups_to_memory_async(
-        self, *, prompt_groups: Sequence[SeedGroup], added_by: Optional[str] = None
+        self, *, prompt_groups: Sequence[SeedGroup], added_by: str | None = None
     ) -> None:
         """
         Insert a list of seed groups into the memory storage.
@@ -1481,21 +1479,21 @@ async def add_seed_groups_to_memory_async(
     def get_seed_groups(
         self,
         *,
-        value: Optional[str] = None,
-        value_sha256: Optional[Sequence[str]] = None,
-        dataset_name: Optional[str] = None,
-        dataset_name_pattern: Optional[str] = None,
-        data_types: Optional[Sequence[str]] = None,
-        harm_categories: Optional[Sequence[str]] = None,
-        added_by: Optional[str] = None,
-        authors: Optional[Sequence[str]] = None,
-        groups: Optional[Sequence[str]] = None,
-        source: Optional[str] = None,
-        seed_type: Optional[SeedType] = None,
-        parameters: Optional[Sequence[str]] = None,
-        metadata: Optional[dict[str, Union[str, int]]] = None,
-        prompt_group_ids: Optional[Sequence[uuid.UUID]] = None,
-        group_length: Optional[Sequence[int]] = None,
+        value: str | None = None,
+        value_sha256: Sequence[str] | None = None,
+        dataset_name: str | None = None,
+        dataset_name_pattern: str | None = None,
+        data_types: Sequence[str] | None = None,
+        harm_categories: Sequence[str] | None = None,
+        added_by: str | None = None,
+        authors: Sequence[str] | None = None,
+        groups: Sequence[str] | None = None,
+        source: str | None = None,
+        seed_type: SeedType | None = None,
+        parameters: Sequence[str] | None = None,
+        metadata: dict[str, str | int] | None = None,
+        prompt_group_ids: Sequence[uuid.UUID] | None = None,
+        group_length: Sequence[int] | None = None,
     ) -> Sequence[SeedGroup]:
         """
         Retrieve groups of seed prompts based on the provided filtering criteria.
@@ -1564,18 +1562,18 @@ def get_seed_groups(
     def export_conversations(
         self,
         *,
-        attack_id: Optional[str | uuid.UUID] = None,
-        conversation_id: Optional[str | uuid.UUID] = None,
-        prompt_ids: Optional[Sequence[str] | Sequence[uuid.UUID]] = None,
-        labels: Optional[dict[str, str]] = None,
-        sent_after: Optional[datetime] = None,
-        sent_before: Optional[datetime] = None,
-        original_values: Optional[Sequence[str]] = None,
-        converted_values: Optional[Sequence[str]] = None,
-        data_type: Optional[str] = None,
-        not_data_type: Optional[str] = None,
-        converted_value_sha256: Optional[Sequence[str]] = None,
-        file_path: Optional[Path] = None,
+        attack_id: str | uuid.UUID | None = None,
+        conversation_id: str | uuid.UUID | None = None,
+        prompt_ids: Sequence[str] | Sequence[uuid.UUID] | None = None,
+        labels: dict[str, str] | None = None,
+        sent_after: datetime | None = None,
+        sent_before: datetime | None = None,
+        original_values: Sequence[str] | None = None,
+        converted_values: Sequence[str] | None = None,
+        data_type: str | None = None,
+        not_data_type: str | None = None,
+        converted_value_sha256: Sequence[str] | None = None,
+        file_path: Path | None = None,
         export_type: str = "json",
     ) -> Path:
         """
@@ -1715,21 +1713,21 @@ def update_attack_result_by_id(self, *, attack_result_id: str, update_fields: di
     def get_attack_results(
         self,
         *,
-        attack_result_ids: Optional[Sequence[str]] = None,
-        conversation_id: Optional[str] = None,
-        objective: Optional[str] = None,
-        objective_sha256: Optional[Sequence[str]] = None,
-        outcome: Optional[str] = None,
-        attack_class: Optional[str] = None,
-        attack_classes: Optional[Sequence[str]] = None,
-        atomic_attack_eval_hashes: Optional[Sequence[str]] = None,
-        converter_classes: Optional[Sequence[str]] = None,
+        attack_result_ids: Sequence[str] | None = None,
+        conversation_id: str | None = None,
+        objective: str | None = None,
+        objective_sha256: Sequence[str] | None = None,
+        outcome: str | None = None,
+        attack_class: str | None = None,
+        attack_classes: Sequence[str] | None = None,
+        atomic_attack_eval_hashes: Sequence[str] | None = None,
+        converter_classes: Sequence[str] | None = None,
         converter_classes_match: Literal["all", "any"] = "all",
-        has_converters: Optional[bool] = None,
-        targeted_harm_categories: Optional[Sequence[str]] = None,
-        labels: Optional[dict[str, str | Sequence[str]]] = None,
-        identifier_filters: Optional[Sequence[IdentifierFilter]] = None,
-        scenario_result_id: Optional[str] = None,
+        has_converters: bool | None = None,
+        targeted_harm_categories: Sequence[str] | None = None,
+        labels: dict[str, str | Sequence[str]] | None = None,
+        identifier_filters: Sequence[IdentifierFilter] | None = None,
+        scenario_result_id: str | None = None,
     ) -> Sequence[AttackResult]:
         """
         Retrieve a list of AttackResult objects based on the specified filters.
@@ -2091,16 +2089,16 @@ def update_scenario_metadata(
     def get_scenario_results(
         self,
         *,
-        scenario_result_ids: Optional[Sequence[str]] = None,
-        scenario_name: Optional[str] = None,
-        scenario_version: Optional[int] = None,
-        pyrit_version: Optional[str] = None,
-        added_after: Optional[datetime] = None,
-        added_before: Optional[datetime] = None,
-        labels: Optional[dict[str, str]] = None,
-        objective_target_endpoint: Optional[str] = None,
-        objective_target_model_name: Optional[str] = None,
-        identifier_filters: Optional[Sequence[IdentifierFilter]] = None,
+        scenario_result_ids: Sequence[str] | None = None,
+        scenario_name: str | None = None,
+        scenario_version: int | None = None,
+        pyrit_version: str | None = None,
+        added_after: datetime | None = None,
+        added_before: datetime | None = None,
+        labels: dict[str, str] | None = None,
+        objective_target_endpoint: str | None = None,
+        objective_target_model_name: str | None = None,
+        identifier_filters: Sequence[IdentifierFilter] | None = None,
         limit: int | None = None,
     ) -> Sequence[ScenarioResult]:
         """
diff --git a/pyrit/memory/sqlite_memory.py b/pyrit/memory/sqlite_memory.py
index 461d2b871b..fef14c2471 100644
--- a/pyrit/memory/sqlite_memory.py
+++ b/pyrit/memory/sqlite_memory.py
@@ -8,7 +8,7 @@
 from contextlib import closing, suppress
 from datetime import datetime
 from pathlib import Path
-from typing import Any, Literal, Optional, TypeVar, Union, cast
+from typing import Any, Literal, TypeVar, cast
 
 from sqlalchemy import and_, create_engine, exists, func, or_, text
 from sqlalchemy.engine.base import Engine
@@ -59,7 +59,7 @@ class SQLiteMemory(MemoryInterface, metaclass=Singleton):
     def __init__(
         self,
         *,
-        db_path: Optional[Union[Path, str]] = None,
+        db_path: Path | str | None = None,
         verbose: bool = False,
         skip_schema_migration: bool = False,
         silent: bool = False,
@@ -80,7 +80,7 @@ def __init__(
         super().__init__()
 
         if db_path == ":memory:":
-            self.db_path: Union[Path, str] = ":memory:"
+            self.db_path: Path | str = ":memory:"
         else:
             self.db_path = Path(db_path or Path(DB_DATA_PATH, self.DEFAULT_DB_FILE_NAME)).resolve()
         self.results_path = str(DB_DATA_PATH)
@@ -179,7 +179,7 @@ def _get_message_pieces_memory_label_conditions(self, *, memory_labels: dict[str
         return [or_(pme_match, are_match)]
 
     def _get_message_pieces_prompt_metadata_conditions(
-        self, *, prompt_metadata: dict[str, Union[str, int]]
+        self, *, prompt_metadata: dict[str, str | int]
     ) -> list[TextClause]:
         """
         Generate SQLAlchemy filter conditions for filtering conversation pieces by prompt metadata.
@@ -195,7 +195,7 @@ def _get_message_pieces_prompt_metadata_conditions(
         condition = text(json_conditions).bindparams(**{key: str(value) for key, value in prompt_metadata.items()})
         return [condition]
 
-    def _get_seed_metadata_conditions(self, *, metadata: dict[str, Union[str, int]]) -> Any:
+    def _get_seed_metadata_conditions(self, *, metadata: dict[str, str | int]) -> Any:
         """
         Generate SQLAlchemy filter conditions for filtering seed prompts by metadata.
 
@@ -334,10 +334,10 @@ def _query_entries(
         self,
         model_class: type[Model],
         *,
-        conditions: Optional[Any] = None,
+        conditions: Any | None = None,
         distinct: bool = False,
         join_scores: bool = False,
-        order_by: Optional[Any] = None,
+        order_by: Any | None = None,
         limit: int | None = None,
     ) -> MutableSequence[Model]:
         """
@@ -487,18 +487,18 @@ def dispose_engine(self) -> None:
     def export_conversations(
         self,
         *,
-        attack_id: Optional[str | uuid.UUID] = None,
-        conversation_id: Optional[str | uuid.UUID] = None,
-        prompt_ids: Optional[Sequence[str] | Sequence[uuid.UUID]] = None,
-        labels: Optional[dict[str, str]] = None,
-        sent_after: Optional[datetime] = None,
-        sent_before: Optional[datetime] = None,
-        original_values: Optional[Sequence[str]] = None,
-        converted_values: Optional[Sequence[str]] = None,
-        data_type: Optional[str] = None,
-        not_data_type: Optional[str] = None,
-        converted_value_sha256: Optional[Sequence[str]] = None,
-        file_path: Optional[Path] = None,
+        attack_id: str | uuid.UUID | None = None,
+        conversation_id: str | uuid.UUID | None = None,
+        prompt_ids: Sequence[str] | Sequence[uuid.UUID] | None = None,
+        labels: dict[str, str] | None = None,
+        sent_after: datetime | None = None,
+        sent_before: datetime | None = None,
+        original_values: Sequence[str] | None = None,
+        converted_values: Sequence[str] | None = None,
+        data_type: str | None = None,
+        not_data_type: str | None = None,
+        converted_value_sha256: Sequence[str] | None = None,
+        file_path: Path | None = None,
         export_type: str = "json",
     ) -> Path:
         """
diff --git a/pyrit/message_normalizer/chat_message_normalizer.py b/pyrit/message_normalizer/chat_message_normalizer.py
index 4fc11fbd0a..d3fcaade31 100644
--- a/pyrit/message_normalizer/chat_message_normalizer.py
+++ b/pyrit/message_normalizer/chat_message_normalizer.py
@@ -4,7 +4,7 @@
 import base64
 import json
 from pathlib import Path
-from typing import TYPE_CHECKING, Any, Union
+from typing import TYPE_CHECKING, Any
 
 import aiofiles
 
@@ -93,7 +93,7 @@ async def normalize_async(self, messages: list[Message]) -> list[ChatMessage]:
 
             # Use simple string for single text piece, otherwise use content list
             if len(pieces) == 1 and pieces[0].converted_value_data_type == "text":
-                content: Union[str, list[dict[str, Any]]] = pieces[0].converted_value
+                content: str | list[dict[str, Any]] = pieces[0].converted_value
             else:
                 content = [await self._piece_to_content_dict_async(piece) for piece in pieces]
 
diff --git a/pyrit/message_normalizer/tokenizer_template_normalizer.py b/pyrit/message_normalizer/tokenizer_template_normalizer.py
index caab9fa337..06c904505b 100644
--- a/pyrit/message_normalizer/tokenizer_template_normalizer.py
+++ b/pyrit/message_normalizer/tokenizer_template_normalizer.py
@@ -2,7 +2,7 @@
 # Licensed under the MIT license.
 import logging
 from dataclasses import dataclass
-from typing import TYPE_CHECKING, ClassVar, Literal, Optional, cast
+from typing import TYPE_CHECKING, ClassVar, Literal, cast
 
 from pyrit.common import get_non_required_value
 from pyrit.message_normalizer.chat_message_normalizer import ChatMessageNormalizer
@@ -109,7 +109,7 @@ def __init__(
         self.system_message_behavior = system_message_behavior
 
     @staticmethod
-    def _load_tokenizer(model_name: str, token: Optional[str]) -> "PreTrainedTokenizerBase":
+    def _load_tokenizer(model_name: str, token: str | None) -> "PreTrainedTokenizerBase":
         """
         Load a tokenizer from HuggingFace.
 
@@ -134,8 +134,8 @@ def from_model(
         cls,
         model_name_or_alias: str,
         *,
-        token: Optional[str] = None,
-        system_message_behavior: Optional[TokenizerSystemBehavior] = None,
+        token: str | None = None,
+        system_message_behavior: TokenizerSystemBehavior | None = None,
     ) -> "TokenizerTemplateNormalizer":
         """
         Create a normalizer from a model name or alias.
diff --git a/pyrit/models/chat_message.py b/pyrit/models/chat_message.py
index c2f801862d..b873b33333 100644
--- a/pyrit/models/chat_message.py
+++ b/pyrit/models/chat_message.py
@@ -1,7 +1,7 @@
 # Copyright (c) Microsoft Corporation.
 # Licensed under the MIT license.
 
-from typing import Any, Optional, Union
+from typing import Any
 
 from pydantic import BaseModel, ConfigDict
 
@@ -30,10 +30,10 @@ class ChatMessage(BaseModel):
 
     model_config = ConfigDict(extra="forbid")
     role: ChatMessageRole
-    content: Union[str, list[dict[str, Any]]]
-    name: Optional[str] = None
-    tool_calls: Optional[list[ToolCall]] = None
-    tool_call_id: Optional[str] = None
+    content: str | list[dict[str, Any]]
+    name: str | None = None
+    tool_calls: list[ToolCall] | None = None
+    tool_call_id: str | None = None
 
     def to_dict(self) -> dict[str, Any]:
         """
diff --git a/pyrit/models/conversation_reference.py b/pyrit/models/conversation_reference.py
index 0915a045c4..6e39cfd233 100644
--- a/pyrit/models/conversation_reference.py
+++ b/pyrit/models/conversation_reference.py
@@ -4,7 +4,6 @@
 from __future__ import annotations
 
 from enum import Enum
-from typing import Optional
 
 from pydantic import BaseModel, ConfigDict
 
@@ -27,7 +26,7 @@ class ConversationReference(BaseModel):
 
     conversation_id: str
     conversation_type: ConversationType
-    description: Optional[str] = None
+    description: str | None = None
 
     def __hash__(self) -> int:
         """
diff --git a/pyrit/models/conversation_stats.py b/pyrit/models/conversation_stats.py
index 67b09e24be..14497954f5 100644
--- a/pyrit/models/conversation_stats.py
+++ b/pyrit/models/conversation_stats.py
@@ -2,7 +2,7 @@
 # Licensed under the MIT license.
 
 from datetime import datetime
-from typing import ClassVar, Optional
+from typing import ClassVar
 
 from pydantic import BaseModel, ConfigDict, Field
 
@@ -29,7 +29,7 @@ class ConversationStats(BaseModel):
     """
 
     message_count: int = 0
-    last_message_preview: Optional[str] = None
-    last_message_data_type: Optional[PromptDataType] = None
+    last_message_preview: str | None = None
+    last_message_data_type: PromptDataType | None = None
     labels: dict[str, str] = Field(default_factory=dict)
-    created_at: Optional[datetime] = None
+    created_at: datetime | None = None
diff --git a/pyrit/models/data_type_serializer.py b/pyrit/models/data_type_serializer.py
index 3ee43eed62..3d529472fc 100644
--- a/pyrit/models/data_type_serializer.py
+++ b/pyrit/models/data_type_serializer.py
@@ -11,7 +11,7 @@
 import wave
 from mimetypes import guess_type
 from pathlib import Path
-from typing import TYPE_CHECKING, Literal, Optional, Union, get_args
+from typing import TYPE_CHECKING, Literal, get_args
 from urllib.parse import urlparse
 
 import aiofiles
@@ -47,8 +47,8 @@ def _write_wav_sync(
 def data_serializer_factory(
     *,
     data_type: PromptDataType,
-    value: Optional[str] = None,
-    extension: Optional[str] = None,
+    value: str | None = None,
+    extension: str | None = None,
     category: AllowedCategories,
 ) -> DataTypeSerializer:
     """
@@ -113,7 +113,7 @@ class DataTypeSerializer(abc.ABC):
     data_sub_directory: str
     file_extension: str
 
-    _file_path: Union[Path, str] | None = None
+    _file_path: Path | str | None = None
 
     @property
     def _memory(self) -> MemoryInterface:
@@ -151,7 +151,7 @@ def data_on_disk(self) -> bool:
 
         """
 
-    async def save_data_async(self, data: bytes, output_filename: Optional[str] = None) -> None:
+    async def save_data_async(self, data: bytes, output_filename: str | None = None) -> None:
         """
         Save data to storage.
 
@@ -192,7 +192,7 @@ async def save_formatted_audio_async(
         num_channels: int = 1,
         sample_width: int = 2,
         sample_rate: int = 16000,
-        output_filename: Optional[str] = None,
+        output_filename: str | None = None,
     ) -> None:
         """
         Save PCM16 or similarly formatted audio data to storage.
@@ -310,7 +310,7 @@ async def get_sha256_async(self) -> str:
         hash_object = hashlib.sha256(input_bytes)
         return hash_object.hexdigest()
 
-    async def get_data_filename_async(self, file_name: Optional[str] = None) -> Union[Path, str]:
+    async def get_data_filename_async(self, file_name: str | None = None) -> Path | str:
         """
         Generate or retrieve a unique filename for the data file.
 
@@ -356,7 +356,7 @@ async def get_data_filename_async(self, file_name: Optional[str] = None) -> Unio
         return self._file_path
 
     async def save_data(  # pyrit-async-suffix-exempt
-        self, data: bytes, output_filename: Optional[str] = None
+        self, data: bytes, output_filename: str | None = None
     ) -> None:
         """
         Save data to storage (deprecated alias of ``save_data_async``).
@@ -395,7 +395,7 @@ async def save_formatted_audio(  # pyrit-async-suffix-exempt
         num_channels: int = 1,
         sample_width: int = 2,
         sample_rate: int = 16000,
-        output_filename: Optional[str] = None,
+        output_filename: str | None = None,
     ) -> None:
         """
         Save formatted audio data to storage (deprecated alias of ``save_formatted_audio_async``).
@@ -457,8 +457,8 @@ async def get_sha256(self) -> str:  # pyrit-async-suffix-exempt
         return await self.get_sha256_async()
 
     async def get_data_filename(  # pyrit-async-suffix-exempt
-        self, file_name: Optional[str] = None
-    ) -> Union[Path, str]:
+        self, file_name: str | None = None
+    ) -> Path | str:
         """
         Generate or retrieve a unique filename for the data file (deprecated alias of ``get_data_filename_async``).
 
@@ -574,7 +574,7 @@ def data_on_disk(self) -> bool:
 class URLDataTypeSerializer(DataTypeSerializer):
     """Serializer for URL values and URL-backed local file references."""
 
-    def __init__(self, *, category: str, prompt_text: str, extension: Optional[str] = None) -> None:
+    def __init__(self, *, category: str, prompt_text: str, extension: str | None = None) -> None:
         """
         Initialize a URL serializer.
 
@@ -604,7 +604,7 @@ def data_on_disk(self) -> bool:
 class ImagePathDataTypeSerializer(DataTypeSerializer):
     """Serializer for image path values stored on disk."""
 
-    def __init__(self, *, category: str, prompt_text: Optional[str] = None, extension: Optional[str] = None) -> None:
+    def __init__(self, *, category: str, prompt_text: str | None = None, extension: str | None = None) -> None:
         """
         Initialize an image-path serializer.
 
@@ -639,8 +639,8 @@ def __init__(
         self,
         *,
         category: str,
-        prompt_text: Optional[str] = None,
-        extension: Optional[str] = None,
+        prompt_text: str | None = None,
+        extension: str | None = None,
     ) -> None:
         """
         Initialize an audio-path serializer.
@@ -676,8 +676,8 @@ def __init__(
         self,
         *,
         category: str,
-        prompt_text: Optional[str] = None,
-        extension: Optional[str] = None,
+        prompt_text: str | None = None,
+        extension: str | None = None,
     ) -> None:
         """
         Initialize a video-path serializer.
@@ -713,8 +713,8 @@ def __init__(
         self,
         *,
         category: str,
-        prompt_text: Optional[str] = None,
-        extension: Optional[str] = None,
+        prompt_text: str | None = None,
+        extension: str | None = None,
     ) -> None:
         """
         Initialize a generic binary-path serializer.
diff --git a/pyrit/models/harm_definition.py b/pyrit/models/harm_definition.py
index 9e739244ab..6e74d6aef9 100644
--- a/pyrit/models/harm_definition.py
+++ b/pyrit/models/harm_definition.py
@@ -10,7 +10,6 @@
 import logging
 import re
 from pathlib import Path
-from typing import Optional, Union
 
 import yaml
 from pydantic import BaseModel, Field
@@ -53,9 +52,9 @@ class HarmDefinition(BaseModel):
     version: str
     category: str
     scale_descriptions: list[ScaleDescription] = Field(default_factory=list)
-    source_path: Optional[str] = None
+    source_path: str | None = None
 
-    def get_scale_description(self, score_value: str) -> Optional[str]:
+    def get_scale_description(self, score_value: str) -> str | None:
         """
         Get the description for a specific score value.
 
@@ -101,7 +100,7 @@ def validate_category(category: str, *, check_exists: bool = False) -> bool:
         return True
 
     @classmethod
-    def from_yaml(cls, harm_definition_path: Union[str, Path]) -> "HarmDefinition":
+    def from_yaml(cls, harm_definition_path: str | Path) -> "HarmDefinition":
         """
         Load and validate a harm definition from a YAML file.
 
diff --git a/pyrit/models/identifiers/component_identifier.py b/pyrit/models/identifiers/component_identifier.py
index d3d0c71933..f050e6e67e 100644
--- a/pyrit/models/identifiers/component_identifier.py
+++ b/pyrit/models/identifiers/component_identifier.py
@@ -20,7 +20,7 @@
 import json
 import logging
 from abc import ABC, abstractmethod
-from typing import Any, ClassVar, Optional, Union
+from typing import Any, ClassVar
 
 from pydantic import BaseModel, ConfigDict, Field, SerializationInfo, model_serializer, model_validator
 
@@ -162,16 +162,16 @@ class ComponentIdentifier(BaseModel):
     #: Behavioral parameters that affect output.
     params: dict[str, Any] = Field(default_factory=dict)
     #: Named child identifiers for compositional identity (e.g., a scorer's target).
-    children: dict[str, Union[ComponentIdentifier, list[ComponentIdentifier]]] = Field(default_factory=dict)
+    children: dict[str, ComponentIdentifier | list[ComponentIdentifier]] = Field(default_factory=dict)
     #: Content-addressed SHA256 hash. Computed automatically when ``None``;
     #: pass an explicit value to preserve a hash from DB storage where params
     #: may have been truncated.
-    hash: Optional[str] = None
+    hash: str | None = None
     #: Version tag for storage. Not included in the content hash.
     pyrit_version: str = Field(default=pyrit.__version__)
     #: Evaluation hash. Computed by EvaluationIdentifier subclasses and attached
     #: to the identifier so it survives DB round-trips with truncated params.
-    eval_hash: Optional[str] = None
+    eval_hash: str | None = None
 
     # ------------------------------------------------------------------
     # Validators
@@ -435,8 +435,8 @@ def of(
         cls,
         obj: object,
         *,
-        params: Optional[dict[str, Any]] = None,
-        children: Optional[dict[str, Union[ComponentIdentifier, list[ComponentIdentifier]]]] = None,
+        params: dict[str, Any] | None = None,
+        children: dict[str, ComponentIdentifier | list[ComponentIdentifier]] | None = None,
     ) -> ComponentIdentifier:
         """
         Build a ComponentIdentifier from a live object instance.
@@ -464,7 +464,7 @@ def of(
             children=clean_children,
         )
 
-    def get_child(self, key: str) -> Optional[ComponentIdentifier]:
+    def get_child(self, key: str) -> ComponentIdentifier | None:
         """
         Get a single child by key.
 
@@ -519,7 +519,7 @@ def _collect_child_eval_hashes(self) -> set[str]:
         return hashes
 
     @staticmethod
-    def _truncate_value(*, value: Any, max_length: Optional[int]) -> Any:
+    def _truncate_value(*, value: Any, max_length: int | None) -> Any:
         """
         Truncate string values longer than ``max_length`` with a ``...`` suffix.
 
@@ -538,7 +538,7 @@ def _truncate_value(*, value: Any, max_length: Optional[int]) -> Any:
     # Deprecated shims — kept for one release cycle
     # ------------------------------------------------------------------
 
-    def to_dict(self, *, max_value_length: Optional[int] = None) -> dict[str, Any]:
+    def to_dict(self, *, max_value_length: int | None = None) -> dict[str, Any]:
         """
         Return the flat storage dict (deprecated; use ``model_dump`` instead).
 
@@ -584,7 +584,7 @@ class Identifiable(ABC):
     component's lifetime.
     """
 
-    _identifier: Optional[ComponentIdentifier] = None
+    _identifier: ComponentIdentifier | None = None
 
     @abstractmethod
     def _build_identifier(self) -> ComponentIdentifier:
diff --git a/pyrit/models/identifiers/evaluation_identifier.py b/pyrit/models/identifiers/evaluation_identifier.py
index b2fc1b996d..27ed3a2cac 100644
--- a/pyrit/models/identifiers/evaluation_identifier.py
+++ b/pyrit/models/identifiers/evaluation_identifier.py
@@ -23,7 +23,7 @@
 from __future__ import annotations
 
 from abc import ABC
-from typing import TYPE_CHECKING, Any, ClassVar, Optional
+from typing import TYPE_CHECKING, Any, ClassVar
 
 from pydantic import BaseModel, ConfigDict, Field
 
@@ -65,18 +65,18 @@ class ChildEvalRule(BaseModel):
     model_config = ConfigDict(frozen=True)
 
     exclude: bool = False
-    included_params: Optional[frozenset[str]] = None
-    included_item_values: Optional[dict[str, Any]] = Field(default=None)
-    param_fallbacks: Optional[dict[str, str]] = Field(default=None)
-    inner_child_name: Optional[str] = Field(default=None)
+    included_params: frozenset[str] | None = None
+    included_item_values: dict[str, Any] | None = Field(default=None)
+    param_fallbacks: dict[str, str] | None = Field(default=None)
+    inner_child_name: str | None = Field(default=None)
 
 
 def _build_eval_dict(
     identifier: ComponentIdentifier,
     *,
     child_eval_rules: dict[str, ChildEvalRule],
-    _included_params: Optional[frozenset[str]] = None,
-    _param_fallbacks: Optional[dict[str, str]] = None,
+    _included_params: frozenset[str] | None = None,
+    _param_fallbacks: dict[str, str] | None = None,
 ) -> dict[str, Any]:
     """
     Build a filtered dictionary for eval-hash computation.
@@ -177,7 +177,7 @@ def compute_eval_hash(
     identifier: ComponentIdentifier,
     *,
     child_eval_rules: dict[str, ChildEvalRule],
-    own_rule: Optional[ChildEvalRule] = None,
+    own_rule: ChildEvalRule | None = None,
 ) -> str:
     """
     Compute a behavioral equivalence hash for evaluation grouping.
@@ -252,7 +252,7 @@ class EvaluationIdentifier(ABC):
     """
 
     CHILD_EVAL_RULES: ClassVar[dict[str, ChildEvalRule]]
-    OWN_RULE: ClassVar[Optional[ChildEvalRule]] = None
+    OWN_RULE: ClassVar[ChildEvalRule | None] = None
 
     def __init__(self, identifier: ComponentIdentifier) -> None:
         """
@@ -357,7 +357,7 @@ class ObjectiveTargetEvaluationIdentifier(EvaluationIdentifier):
     """
 
     CHILD_EVAL_RULES: ClassVar[dict[str, ChildEvalRule]] = {}
-    OWN_RULE: ClassVar[Optional[ChildEvalRule]] = ChildEvalRule(
+    OWN_RULE: ClassVar[ChildEvalRule | None] = ChildEvalRule(
         included_params=TARGET_EVAL_PARAMS,
         param_fallbacks=TARGET_EVAL_PARAM_FALLBACKS,
     )
diff --git a/pyrit/models/json_response_config.py b/pyrit/models/json_response_config.py
index 8c4c1b9864..b6915526b3 100644
--- a/pyrit/models/json_response_config.py
+++ b/pyrit/models/json_response_config.py
@@ -4,7 +4,7 @@
 from __future__ import annotations
 
 import json
-from typing import Any, Optional
+from typing import Any
 
 from pydantic import BaseModel, ConfigDict
 
@@ -30,12 +30,12 @@ class _JsonResponseConfig(BaseModel):
     model_config = ConfigDict(extra="forbid")
 
     enabled: bool = False
-    json_schema: Optional[dict[str, Any]] = None
+    json_schema: dict[str, Any] | None = None
     schema_name: str = "CustomSchema"
     strict: bool = True
 
     @classmethod
-    def from_metadata(cls, *, metadata: Optional[dict[str, Any]]) -> _JsonResponseConfig:
+    def from_metadata(cls, *, metadata: dict[str, Any] | None) -> _JsonResponseConfig:
         if not metadata:
             return cls(enabled=False)
 
diff --git a/pyrit/models/messages/conversations.py b/pyrit/models/messages/conversations.py
index 2b5224f6c6..6b625ac46c 100644
--- a/pyrit/models/messages/conversations.py
+++ b/pyrit/models/messages/conversations.py
@@ -5,7 +5,7 @@
 
 from __future__ import annotations
 
-from typing import TYPE_CHECKING, Optional, Union
+from typing import TYPE_CHECKING
 
 from pyrit.models.messages.message import Message
 from pyrit.models.messages.message_piece import MessagePiece
@@ -178,7 +178,7 @@ def construct_response_from_request(
     request: MessagePiece,
     response_text_pieces: list[str],
     response_type: PromptDataType = "text",
-    prompt_metadata: Optional[dict[str, Union[str, int]]] = None,
+    prompt_metadata: dict[str, str | int] | None = None,
     error: PromptResponseError = "none",
 ) -> Message:
     """
diff --git a/pyrit/models/messages/message.py b/pyrit/models/messages/message.py
index d14f1ec1b9..91f208d8d9 100644
--- a/pyrit/models/messages/message.py
+++ b/pyrit/models/messages/message.py
@@ -6,7 +6,7 @@
 import copy
 import uuid
 from datetime import datetime, timezone
-from typing import TYPE_CHECKING, Any, Optional, Union
+from typing import TYPE_CHECKING, Any
 
 from pydantic import BaseModel, ConfigDict, model_validator
 
@@ -195,9 +195,9 @@ def get_piece(self, n: int = 0) -> MessagePiece:
     def get_pieces_by_type(
         self,
         *,
-        data_type: Optional[PromptDataType] = None,
-        original_value_data_type: Optional[PromptDataType] = None,
-        converted_value_data_type: Optional[PromptDataType] = None,
+        data_type: PromptDataType | None = None,
+        original_value_data_type: PromptDataType | None = None,
+        converted_value_data_type: PromptDataType | None = None,
     ) -> list[MessagePiece]:
         """
         Return all message pieces matching the given data type.
@@ -222,10 +222,10 @@ def get_pieces_by_type(
     def get_piece_by_type(
         self,
         *,
-        data_type: Optional[PromptDataType] = None,
-        original_value_data_type: Optional[PromptDataType] = None,
-        converted_value_data_type: Optional[PromptDataType] = None,
-    ) -> Optional[MessagePiece]:
+        data_type: PromptDataType | None = None,
+        original_value_data_type: PromptDataType | None = None,
+        converted_value_data_type: PromptDataType | None = None,
+    ) -> MessagePiece | None:
         """
         Return the first message piece matching the given data type, or None.
 
@@ -358,7 +358,7 @@ def from_prompt(
         *,
         prompt: str,
         role: ChatMessageRole,
-        prompt_metadata: Optional[dict[str, Union[str, int]]] = None,
+        prompt_metadata: dict[str, str | int] | None = None,
     ) -> Message:
         """
         Build a single-piece message from prompt text.
diff --git a/pyrit/models/messages/message_piece.py b/pyrit/models/messages/message_piece.py
index 131919ecf8..0649a08e77 100644
--- a/pyrit/models/messages/message_piece.py
+++ b/pyrit/models/messages/message_piece.py
@@ -5,7 +5,7 @@
 
 import uuid
 from datetime import datetime, timezone
-from typing import TYPE_CHECKING, Any, Literal, Optional
+from typing import TYPE_CHECKING, Any, Literal
 from uuid import uuid4
 
 from pydantic import (
@@ -102,20 +102,20 @@ class MessagePiece(BaseModel):
     timestamp: AwareDatetime = Field(default_factory=lambda: datetime.now(tz=timezone.utc))
     original_value: str
     original_value_data_type: PromptDataType = "text"
-    original_value_sha256: Optional[str] = None
+    original_value_sha256: str | None = None
     converted_value: str = ""
     converted_value_data_type: PromptDataType = "text"
-    converted_value_sha256: Optional[str] = None
+    converted_value_sha256: str | None = None
     response_error: PromptResponseError = "none"
     originator: Literal["attack", "converter", "undefined", "scorer"] = "undefined"
-    original_prompt_id: Optional[uuid.UUID] = None
+    original_prompt_id: uuid.UUID | None = None
     labels: dict[str, Any] = Field(default_factory=dict)
     targeted_harm_categories: list[str] = Field(default_factory=list)
     prompt_metadata: dict[str, Any] = Field(default_factory=dict)
     converter_identifiers: list[ComponentIdentifierField] = Field(default_factory=list)
-    prompt_target_identifier: Optional[ComponentIdentifierField] = None
-    attack_identifier: Optional[ComponentIdentifierField] = None
-    scorer_identifier: Optional[ComponentIdentifierField] = None
+    prompt_target_identifier: ComponentIdentifierField | None = None
+    attack_identifier: ComponentIdentifierField | None = None
+    scorer_identifier: ComponentIdentifierField | None = None
     scores: list[Score] = Field(default_factory=list)
 
     # When True, the memory layer skips persisting this piece. Used for ephemeral
diff --git a/pyrit/models/question_answering.py b/pyrit/models/question_answering.py
index c468461090..8e1ca76e0f 100644
--- a/pyrit/models/question_answering.py
+++ b/pyrit/models/question_answering.py
@@ -3,7 +3,7 @@
 
 from __future__ import annotations
 
-from typing import Literal, Union
+from typing import Literal
 
 from pydantic import BaseModel, ConfigDict
 
@@ -26,7 +26,7 @@ class QuestionAnsweringEntry(BaseModel):
     model_config = ConfigDict(extra="forbid")
     question: str
     answer_type: Literal["int", "float", "str", "bool"]
-    correct_answer: Union[int, str, float]
+    correct_answer: int | str | float
     choices: list[QuestionChoice]
 
     def get_correct_answer_text(self) -> str:
diff --git a/pyrit/models/retry_event.py b/pyrit/models/retry_event.py
index 46a6e79fcf..2ef67f908f 100644
--- a/pyrit/models/retry_event.py
+++ b/pyrit/models/retry_event.py
@@ -6,7 +6,6 @@
 from __future__ import annotations
 
 from datetime import datetime, timezone
-from typing import Optional
 
 from pydantic import BaseModel, Field
 
@@ -29,8 +28,8 @@ class RetryEvent(BaseModel):
     exception_type: str = ""
     exception_message: str = ""
     component_role: str = ""
-    component_name: Optional[str] = None
-    endpoint: Optional[str] = None
+    component_name: str | None = None
+    endpoint: str | None = None
     elapsed_seconds: float = 0.0
 
     def to_dict(self) -> dict:
diff --git a/pyrit/models/storage_io.py b/pyrit/models/storage_io.py
index 5b610f80d8..09ccd0d70e 100644
--- a/pyrit/models/storage_io.py
+++ b/pyrit/models/storage_io.py
@@ -7,7 +7,7 @@
 from abc import ABC, abstractmethod
 from enum import Enum
 from pathlib import Path
-from typing import TYPE_CHECKING, Optional, Union
+from typing import TYPE_CHECKING
 from urllib.parse import urlparse
 
 import aiofiles
@@ -36,36 +36,36 @@ class StorageIO(ABC):
     """
 
     @abstractmethod
-    async def read_file_async(self, path: Union[Path, str]) -> bytes:
+    async def read_file_async(self, path: Path | str) -> bytes:
         """
         Asynchronously reads the file (or blob) from the given path.
         """
 
     @abstractmethod
-    async def write_file_async(self, path: Union[Path, str], data: bytes) -> None:
+    async def write_file_async(self, path: Path | str, data: bytes) -> None:
         """
         Asynchronously writes data to the given path.
         """
 
     @abstractmethod
-    async def path_exists_async(self, path: Union[Path, str]) -> bool:
+    async def path_exists_async(self, path: Path | str) -> bool:
         """
         Asynchronously checks if a file or blob exists at the given path.
         """
 
     @abstractmethod
-    async def is_file_async(self, path: Union[Path, str]) -> bool:
+    async def is_file_async(self, path: Path | str) -> bool:
         """
         Asynchronously checks if the path refers to a file (not a directory or container).
         """
 
     @abstractmethod
-    async def create_directory_if_not_exists_async(self, path: Union[Path, str]) -> None:
+    async def create_directory_if_not_exists_async(self, path: Path | str) -> None:
         """
         Asynchronously creates a directory or equivalent in the storage system if it doesn't exist.
         """
 
-    async def read_file(self, path: Union[Path, str]) -> bytes:  # pyrit-async-suffix-exempt
+    async def read_file(self, path: Path | str) -> bytes:  # pyrit-async-suffix-exempt
         """
         Read a file from storage (deprecated alias of ``read_file_async``).
 
@@ -82,7 +82,7 @@ async def read_file(self, path: Union[Path, str]) -> bytes:  # pyrit-async-suffi
         )
         return await self.read_file_async(path)
 
-    async def write_file(self, path: Union[Path, str], data: bytes) -> None:  # pyrit-async-suffix-exempt
+    async def write_file(self, path: Path | str, data: bytes) -> None:  # pyrit-async-suffix-exempt
         """
         Write data to storage (deprecated alias of ``write_file_async``).
 
@@ -97,7 +97,7 @@ async def write_file(self, path: Union[Path, str], data: bytes) -> None:  # pyri
         )
         await self.write_file_async(path, data)
 
-    async def path_exists(self, path: Union[Path, str]) -> bool:  # pyrit-async-suffix-exempt
+    async def path_exists(self, path: Path | str) -> bool:  # pyrit-async-suffix-exempt
         """
         Check whether a path exists (deprecated alias of ``path_exists_async``).
 
@@ -114,7 +114,7 @@ async def path_exists(self, path: Union[Path, str]) -> bool:  # pyrit-async-suff
         )
         return await self.path_exists_async(path)
 
-    async def is_file(self, path: Union[Path, str]) -> bool:  # pyrit-async-suffix-exempt
+    async def is_file(self, path: Path | str) -> bool:  # pyrit-async-suffix-exempt
         """
         Check whether the given path is a file (deprecated alias of ``is_file_async``).
 
@@ -131,7 +131,7 @@ async def is_file(self, path: Union[Path, str]) -> bool:  # pyrit-async-suffix-e
         )
         return await self.is_file_async(path)
 
-    async def create_directory_if_not_exists(self, path: Union[Path, str]) -> None:  # pyrit-async-suffix-exempt
+    async def create_directory_if_not_exists(self, path: Path | str) -> None:  # pyrit-async-suffix-exempt
         """
         Create a directory if it does not exist (deprecated alias of ``create_directory_if_not_exists_async``).
 
@@ -151,7 +151,7 @@ class DiskStorageIO(StorageIO):
     Implementation of StorageIO for local disk storage.
     """
 
-    async def read_file_async(self, path: Union[Path, str]) -> bytes:
+    async def read_file_async(self, path: Path | str) -> bytes:
         """
         Asynchronously reads a file from the local disk.
 
@@ -166,7 +166,7 @@ async def read_file_async(self, path: Union[Path, str]) -> bytes:
         async with aiofiles.open(path, "rb") as file:
             return await file.read()
 
-    async def write_file_async(self, path: Union[Path, str], data: bytes) -> None:
+    async def write_file_async(self, path: Path | str, data: bytes) -> None:
         """
         Asynchronously writes data to a file on the local disk.
 
@@ -179,7 +179,7 @@ async def write_file_async(self, path: Union[Path, str], data: bytes) -> None:
         async with aiofiles.open(path, "wb") as file:
             await file.write(data)
 
-    async def path_exists_async(self, path: Union[Path, str]) -> bool:
+    async def path_exists_async(self, path: Path | str) -> bool:
         """
         Check whether a path exists on the local disk.
 
@@ -193,7 +193,7 @@ async def path_exists_async(self, path: Union[Path, str]) -> bool:
         path = self._convert_to_path(path)
         return path.exists()
 
-    async def is_file_async(self, path: Union[Path, str]) -> bool:
+    async def is_file_async(self, path: Path | str) -> bool:
         """
         Check whether the given path is a file (not a directory).
 
@@ -207,7 +207,7 @@ async def is_file_async(self, path: Union[Path, str]) -> bool:
         path = self._convert_to_path(path)
         return path.is_file()
 
-    async def create_directory_if_not_exists_async(self, path: Union[Path, str]) -> None:
+    async def create_directory_if_not_exists_async(self, path: Path | str) -> None:
         """
         Asynchronously creates a directory if it doesn't exist on the local disk.
 
@@ -219,7 +219,7 @@ async def create_directory_if_not_exists_async(self, path: Union[Path, str]) ->
         if not directory_path.exists():
             directory_path.mkdir(parents=True, exist_ok=True)
 
-    def _convert_to_path(self, path: Union[Path, str]) -> Path:
+    def _convert_to_path(self, path: Path | str) -> Path:
         """
         Convert an input path to a Path object.
 
@@ -241,8 +241,8 @@ class AzureBlobStorageIO(StorageIO):
     def __init__(
         self,
         *,
-        container_url: Optional[str] = None,
-        sas_token: Optional[str] = None,
+        container_url: str | None = None,
+        sas_token: str | None = None,
         blob_content_type: SupportedContentType = SupportedContentType.PLAIN_TEXT,
     ) -> None:
         """
@@ -351,7 +351,7 @@ def parse_blob_url(self, file_path: str) -> tuple[str, str]:
             return container_name, blob_name
         raise ValueError("Invalid blob URL")
 
-    def _resolve_blob_name(self, path: Union[Path, str]) -> str:
+    def _resolve_blob_name(self, path: Path | str) -> str:
         """
         Resolve a blob name from either a full blob URL or a relative blob path.
 
@@ -377,7 +377,7 @@ def _resolve_blob_name(self, path: Union[Path, str]) -> str:
         except ValueError:
             return path_str
 
-    async def read_file_async(self, path: Union[Path, str]) -> bytes:
+    async def read_file_async(self, path: Path | str) -> bytes:
         """
         Asynchronously reads the content of a file (blob) from Azure Blob Storage.
 
@@ -420,7 +420,7 @@ async def read_file_async(self, path: Union[Path, str]) -> bytes:
             await self._client_async.close()
             self._client_async = None
 
-    async def write_file_async(self, path: Union[Path, str], data: bytes) -> None:
+    async def write_file_async(self, path: Path | str, data: bytes) -> None:
         """
         Write data to Azure Blob Storage at the specified path.
 
@@ -443,7 +443,7 @@ async def write_file_async(self, path: Union[Path, str], data: bytes) -> None:
             await self._client_async.close()
             self._client_async = None
 
-    async def path_exists_async(self, path: Union[Path, str]) -> bool:
+    async def path_exists_async(self, path: Path | str) -> bool:
         """
         Check whether a given path exists in the Azure Blob Storage container.
 
@@ -468,7 +468,7 @@ async def path_exists_async(self, path: Union[Path, str]) -> bool:
             await self._client_async.close()
             self._client_async = None
 
-    async def is_file_async(self, path: Union[Path, str]) -> bool:
+    async def is_file_async(self, path: Path | str) -> bool:
         """
         Check whether the path refers to a file (blob) in Azure Blob Storage.
 
@@ -493,7 +493,7 @@ async def is_file_async(self, path: Union[Path, str]) -> bool:
             await self._client_async.close()
             self._client_async = None
 
-    async def create_directory_if_not_exists_async(self, directory_path: Union[Path, str]) -> None:  # type: ignore[ty:invalid-method-override]
+    async def create_directory_if_not_exists_async(self, directory_path: Path | str) -> None:  # type: ignore[ty:invalid-method-override]
         """
         Log a no-op directory creation for Azure Blob Storage.
 
diff --git a/pyrit/prompt_converter/add_image_to_video_converter.py b/pyrit/prompt_converter/add_image_to_video_converter.py
index 148f4d5e03..8103df378f 100644
--- a/pyrit/prompt_converter/add_image_to_video_converter.py
+++ b/pyrit/prompt_converter/add_image_to_video_converter.py
@@ -5,7 +5,6 @@
 import contextlib
 import logging
 from pathlib import Path
-from typing import Optional
 
 import numpy as np
 
@@ -38,7 +37,7 @@ class AddImageVideoConverter(PromptConverter):
     def __init__(
         self,
         video_path: str,
-        output_path: Optional[str] = None,
+        output_path: str | None = None,
         img_position: tuple[int, int] = (10, 10),
         img_resize_size: tuple[int, int] = (500, 500),
     ) -> None:
@@ -146,9 +145,9 @@ def _add_image_to_video_sync(
         import cv2
 
         video_path = self._video_path
-        local_temp_path: Optional[Path] = None
-        cap: Optional[cv2.VideoCapture] = None
-        output_video: Optional[cv2.VideoWriter] = None
+        local_temp_path: Path | None = None
+        cap: cv2.VideoCapture | None = None
+        output_video: cv2.VideoWriter | None = None
 
         try:
             if azure_storage_flag:
diff --git a/pyrit/prompt_converter/ask_to_decode_converter.py b/pyrit/prompt_converter/ask_to_decode_converter.py
index 847360e37f..cb6e47d148 100644
--- a/pyrit/prompt_converter/ask_to_decode_converter.py
+++ b/pyrit/prompt_converter/ask_to_decode_converter.py
@@ -2,7 +2,6 @@
 # Licensed under the MIT license.
 
 import random
-from typing import Optional
 
 from pyrit.models import PromptDataType
 from pyrit.prompt_converter.prompt_converter import ConverterResult, PromptConverter
@@ -39,7 +38,7 @@ class AskToDecodeConverter(PromptConverter):
 
     all_templates = garak_templates + extra_templates
 
-    def __init__(self, template: Optional[str] = None, encoding_name: str = "cipher") -> None:
+    def __init__(self, template: str | None = None, encoding_name: str = "cipher") -> None:
         """
         Initialize the converter with a specified encoding name and template.
 
diff --git a/pyrit/prompt_converter/azure_speech_audio_to_text_converter.py b/pyrit/prompt_converter/azure_speech_audio_to_text_converter.py
index 9f355ce158..1d1c6abc3a 100644
--- a/pyrit/prompt_converter/azure_speech_audio_to_text_converter.py
+++ b/pyrit/prompt_converter/azure_speech_audio_to_text_converter.py
@@ -5,7 +5,7 @@
 import logging
 import time
 from collections.abc import Awaitable, Callable
-from typing import TYPE_CHECKING, Any, Optional
+from typing import TYPE_CHECKING, Any
 
 if TYPE_CHECKING:
     import azure.cognitiveservices.speech as speechsdk  # noqa: F401
@@ -47,10 +47,10 @@ class AzureSpeechAudioToTextConverter(PromptConverter):
     def __init__(
         self,
         *,
-        azure_speech_region: Optional[str] = None,
-        azure_speech_key: Optional[str | Callable[[], str | Awaitable[str]]] = None,
-        azure_speech_resource_id: Optional[str] = None,
-        use_entra_auth: Optional[bool] = None,
+        azure_speech_region: str | None = None,
+        azure_speech_key: str | Callable[[], str | Awaitable[str]] | None = None,
+        azure_speech_resource_id: str | None = None,
+        use_entra_auth: bool | None = None,
         recognition_language: str = "en-US",
     ) -> None:
         """
diff --git a/pyrit/prompt_converter/azure_speech_text_to_audio_converter.py b/pyrit/prompt_converter/azure_speech_text_to_audio_converter.py
index ffb8934b36..de0eaa5b2f 100644
--- a/pyrit/prompt_converter/azure_speech_text_to_audio_converter.py
+++ b/pyrit/prompt_converter/azure_speech_text_to_audio_converter.py
@@ -3,7 +3,7 @@
 
 import logging
 from collections.abc import Awaitable, Callable
-from typing import TYPE_CHECKING, Literal, Optional
+from typing import TYPE_CHECKING, Literal
 
 if TYPE_CHECKING:
     import azure.cognitiveservices.speech as speechsdk  # noqa: F401
@@ -48,10 +48,10 @@ class AzureSpeechTextToAudioConverter(PromptConverter):
     def __init__(
         self,
         *,
-        azure_speech_region: Optional[str] = None,
-        azure_speech_key: Optional[str | Callable[[], str | Awaitable[str]]] = None,
-        azure_speech_resource_id: Optional[str] = None,
-        use_entra_auth: Optional[bool] = None,
+        azure_speech_region: str | None = None,
+        azure_speech_key: str | Callable[[], str | Awaitable[str]] | None = None,
+        azure_speech_resource_id: str | None = None,
+        use_entra_auth: bool | None = None,
         synthesis_language: str = "en_US",
         synthesis_voice_name: str = "en-US-AvaNeural",
         output_format: AzureSpeechAudioFormat = "wav",
diff --git a/pyrit/prompt_converter/bin_ascii_converter.py b/pyrit/prompt_converter/bin_ascii_converter.py
index f06971d9ee..e958774942 100644
--- a/pyrit/prompt_converter/bin_ascii_converter.py
+++ b/pyrit/prompt_converter/bin_ascii_converter.py
@@ -2,7 +2,7 @@
 # Licensed under the MIT license.
 
 import binascii
-from typing import Literal, Optional
+from typing import Literal
 
 from pyrit.models import ComponentIdentifier
 from pyrit.prompt_converter.text_selection_strategy import (
@@ -29,8 +29,8 @@ def __init__(
         self,
         *,
         encoding_func: EncodingFunc = "hex",
-        word_selection_strategy: Optional[WordSelectionStrategy] = None,
-        word_split_separator: Optional[str] = " ",
+        word_selection_strategy: WordSelectionStrategy | None = None,
+        word_split_separator: str | None = " ",
     ) -> None:
         """
         Initialize the BinAsciiConverter.
diff --git a/pyrit/prompt_converter/binary_converter.py b/pyrit/prompt_converter/binary_converter.py
index c17ce73234..a1fa402438 100644
--- a/pyrit/prompt_converter/binary_converter.py
+++ b/pyrit/prompt_converter/binary_converter.py
@@ -4,7 +4,7 @@
 from __future__ import annotations
 
 from enum import Enum
-from typing import TYPE_CHECKING, Optional
+from typing import TYPE_CHECKING
 
 from pyrit.prompt_converter.word_level_converter import WordLevelConverter
 
@@ -29,7 +29,7 @@ def __init__(
         self,
         *,
         bits_per_char: BinaryConverter.BitsPerChar = BitsPerChar.BITS_16,
-        word_selection_strategy: Optional[WordSelectionStrategy] = None,
+        word_selection_strategy: WordSelectionStrategy | None = None,
     ) -> None:
         """
         Initialize the converter with the specified bits per character and selection strategy.
diff --git a/pyrit/prompt_converter/charswap_attack_converter.py b/pyrit/prompt_converter/charswap_attack_converter.py
index cf91c75a88..cb7e669e11 100644
--- a/pyrit/prompt_converter/charswap_attack_converter.py
+++ b/pyrit/prompt_converter/charswap_attack_converter.py
@@ -3,7 +3,6 @@
 
 import random
 import string
-from typing import Optional
 
 from pyrit.models import ComponentIdentifier
 from pyrit.prompt_converter.text_selection_strategy import (
@@ -22,7 +21,7 @@ def __init__(
         self,
         *,
         max_iterations: int = 10,
-        word_selection_strategy: Optional[WordSelectionStrategy] = None,
+        word_selection_strategy: WordSelectionStrategy | None = None,
     ) -> None:
         """
         Initialize the converter with the specified parameters.
diff --git a/pyrit/prompt_converter/codechameleon_converter.py b/pyrit/prompt_converter/codechameleon_converter.py
index a8d932ec6a..6079cd18f6 100644
--- a/pyrit/prompt_converter/codechameleon_converter.py
+++ b/pyrit/prompt_converter/codechameleon_converter.py
@@ -7,7 +7,7 @@
 import re
 import textwrap
 from collections.abc import Callable
-from typing import Any, Optional
+from typing import Any
 
 from pyrit.common.path import CONVERTER_SEED_PROMPT_PATH
 from pyrit.models import ComponentIdentifier, PromptDataType, SeedPrompt
@@ -52,8 +52,8 @@ def __init__(
         self,
         *,
         encrypt_type: str,
-        encrypt_function: Optional[Callable[..., Any]] = None,
-        decrypt_function: Optional[Callable[..., Any] | list[Callable[..., Any] | str]] = None,
+        encrypt_function: Callable[..., Any] | None = None,
+        decrypt_function: Callable[..., Any] | list[Callable[..., Any] | str] | None = None,
     ) -> None:
         """
         Initialize the converter with the specified encryption type and optional functions.
@@ -163,10 +163,10 @@ class TreeNode:
 
             def __init__(self, value: str) -> None:
                 self.value = value
-                self.left: Optional[TreeNode] = None
-                self.right: Optional[TreeNode] = None
+                self.left: TreeNode | None = None
+                self.right: TreeNode | None = None
 
-        def build_tree(words: list[str], start: int, end: int) -> Optional[TreeNode]:
+        def build_tree(words: list[str], start: int, end: int) -> TreeNode | None:
             """
             Recursively build a balanced binary tree from a sublist of words.
 
@@ -189,7 +189,7 @@ def build_tree(words: list[str], start: int, end: int) -> Optional[TreeNode]:
 
             return node
 
-        def tree_to_json(node: Optional[TreeNode]) -> Optional[dict[str, Any]]:
+        def tree_to_json(node: TreeNode | None) -> dict[str, Any] | None:
             """
             Convert a tree to a JSON representation.
 
diff --git a/pyrit/prompt_converter/colloquial_wordswap_converter.py b/pyrit/prompt_converter/colloquial_wordswap_converter.py
index e6118a4040..9f8d0a204d 100644
--- a/pyrit/prompt_converter/colloquial_wordswap_converter.py
+++ b/pyrit/prompt_converter/colloquial_wordswap_converter.py
@@ -4,7 +4,6 @@
 import pathlib
 import random
 import re
-from typing import Optional
 
 import yaml
 
@@ -28,8 +27,8 @@ def __init__(
         self,
         *,
         deterministic: bool = False,
-        custom_substitutions: Optional[dict[str, list[str]]] = None,
-        wordswap_path: Optional[str] = None,
+        custom_substitutions: dict[str, list[str]] | None = None,
+        wordswap_path: str | None = None,
     ) -> None:
         """
         Initialize the converter with optional deterministic mode and substitutions source.
diff --git a/pyrit/prompt_converter/denylist_converter.py b/pyrit/prompt_converter/denylist_converter.py
index b9a0ee2c7c..aad3854dcc 100644
--- a/pyrit/prompt_converter/denylist_converter.py
+++ b/pyrit/prompt_converter/denylist_converter.py
@@ -3,7 +3,6 @@
 
 import logging
 import pathlib
-from typing import Optional
 
 from pyrit.common.apply_defaults import REQUIRED_VALUE, apply_defaults
 from pyrit.common.path import CONVERTER_SEED_PROMPT_PATH
@@ -27,7 +26,7 @@ def __init__(
         self,
         *,
         converter_target: PromptTarget = REQUIRED_VALUE,  # type: ignore[ty:invalid-parameter-default]
-        system_prompt_template: Optional[SeedPrompt] = None,
+        system_prompt_template: SeedPrompt | None = None,
         denylist: list[str] | None = None,
     ) -> None:
         """
diff --git a/pyrit/prompt_converter/first_letter_converter.py b/pyrit/prompt_converter/first_letter_converter.py
index ce6058ac68..fa610b54e5 100644
--- a/pyrit/prompt_converter/first_letter_converter.py
+++ b/pyrit/prompt_converter/first_letter_converter.py
@@ -1,7 +1,6 @@
 # Copyright (c) Microsoft Corporation.
 # Licensed under the MIT license.
 
-from typing import Optional
 
 from pyrit.models import ComponentIdentifier
 from pyrit.prompt_converter.text_selection_strategy import WordSelectionStrategy
@@ -18,7 +17,7 @@ def __init__(
         self,
         *,
         letter_separator: str = " ",
-        word_selection_strategy: Optional[WordSelectionStrategy] = None,
+        word_selection_strategy: WordSelectionStrategy | None = None,
     ) -> None:
         """
         Initialize the converter with the specified letter separator and selection strategy.
diff --git a/pyrit/prompt_converter/image_compression_converter.py b/pyrit/prompt_converter/image_compression_converter.py
index 57fc13b856..da8c01e91f 100644
--- a/pyrit/prompt_converter/image_compression_converter.py
+++ b/pyrit/prompt_converter/image_compression_converter.py
@@ -4,7 +4,7 @@
 import base64
 import logging
 from io import BytesIO
-from typing import Any, Literal, Optional
+from typing import Any, Literal
 from urllib.parse import urlparse
 
 import aiohttp
@@ -49,13 +49,13 @@ class ImageCompressionConverter(PromptConverter):
     def __init__(
         self,
         *,
-        output_format: Optional[Literal["JPEG", "PNG", "WEBP"]] = None,
-        quality: Optional[int] = None,
-        optimize: Optional[bool] = None,
-        progressive: Optional[bool] = None,
-        compress_level: Optional[int] = None,
-        lossless: Optional[bool] = None,
-        method: Optional[int] = None,
+        output_format: Literal["JPEG", "PNG", "WEBP"] | None = None,
+        quality: int | None = None,
+        optimize: bool | None = None,
+        progressive: bool | None = None,
+        compress_level: int | None = None,
+        lossless: bool | None = None,
+        method: int | None = None,
         background_color: tuple[int, int, int] = (0, 0, 0),
         min_compression_threshold: int = 1024,
         fallback_to_original: bool = True,
diff --git a/pyrit/prompt_converter/insert_punctuation_converter.py b/pyrit/prompt_converter/insert_punctuation_converter.py
index 833f25d124..2049fb4675 100644
--- a/pyrit/prompt_converter/insert_punctuation_converter.py
+++ b/pyrit/prompt_converter/insert_punctuation_converter.py
@@ -4,7 +4,6 @@
 import random
 import re
 import string
-from typing import Optional
 
 from pyrit.models import ComponentIdentifier, PromptDataType
 from pyrit.prompt_converter.prompt_converter import ConverterResult, PromptConverter
@@ -72,7 +71,7 @@ def _is_valid_punctuation(self, punctuation_list: list[str]) -> bool:
         return all(char in string.punctuation for char in punctuation_list)
 
     async def convert_async(
-        self, *, prompt: str, input_type: PromptDataType = "text", punctuation_list: Optional[list[str]] = None
+        self, *, prompt: str, input_type: PromptDataType = "text", punctuation_list: list[str] | None = None
     ) -> ConverterResult:
         """
         Convert the given prompt by inserting punctuation.
diff --git a/pyrit/prompt_converter/leetspeak_converter.py b/pyrit/prompt_converter/leetspeak_converter.py
index a904d804a7..7d0067aaef 100644
--- a/pyrit/prompt_converter/leetspeak_converter.py
+++ b/pyrit/prompt_converter/leetspeak_converter.py
@@ -2,7 +2,6 @@
 # Licensed under the MIT license.
 
 import random
-from typing import Optional
 
 from pyrit.models import ComponentIdentifier
 from pyrit.prompt_converter.text_selection_strategy import WordSelectionStrategy
@@ -18,8 +17,8 @@ def __init__(
         self,
         *,
         deterministic: bool = True,
-        custom_substitutions: Optional[dict[str, list[str]]] = None,
-        word_selection_strategy: Optional[WordSelectionStrategy] = None,
+        custom_substitutions: dict[str, list[str]] | None = None,
+        word_selection_strategy: WordSelectionStrategy | None = None,
     ) -> None:
         """
         Initialize the converter with optional deterministic mode and custom substitutions.
diff --git a/pyrit/prompt_converter/malicious_question_generator_converter.py b/pyrit/prompt_converter/malicious_question_generator_converter.py
index 7e8b64a0d8..e35270bce3 100644
--- a/pyrit/prompt_converter/malicious_question_generator_converter.py
+++ b/pyrit/prompt_converter/malicious_question_generator_converter.py
@@ -3,7 +3,6 @@
 
 import logging
 import pathlib
-from typing import Optional
 
 from pyrit.common.apply_defaults import REQUIRED_VALUE, apply_defaults
 from pyrit.common.path import CONVERTER_SEED_PROMPT_PATH
@@ -27,7 +26,7 @@ def __init__(
         self,
         *,
         converter_target: PromptTarget = REQUIRED_VALUE,  # type: ignore[ty:invalid-parameter-default]
-        prompt_template: Optional[SeedPrompt] = None,
+        prompt_template: SeedPrompt | None = None,
     ) -> None:
         """
         Initialize the converter with a specific target and template.
diff --git a/pyrit/prompt_converter/math_obfuscation_converter.py b/pyrit/prompt_converter/math_obfuscation_converter.py
index 870d7fc03a..7bc0a9b4f7 100644
--- a/pyrit/prompt_converter/math_obfuscation_converter.py
+++ b/pyrit/prompt_converter/math_obfuscation_converter.py
@@ -3,7 +3,6 @@
 
 import logging
 import random
-from typing import Optional
 
 from pyrit.models import ComponentIdentifier, PromptDataType
 from pyrit.prompt_converter.prompt_converter import ConverterResult, PromptConverter
@@ -44,9 +43,9 @@ def __init__(
         *,
         min_n: int = 2,
         max_n: int = 9,
-        hint: Optional[str] = None,
-        suffix: Optional[str] = None,
-        rng: Optional[random.Random] = None,
+        hint: str | None = None,
+        suffix: str | None = None,
+        rng: random.Random | None = None,
     ) -> None:
         """
         Initialize a MathObfuscationConverter instance.
diff --git a/pyrit/prompt_converter/math_prompt_converter.py b/pyrit/prompt_converter/math_prompt_converter.py
index ce9a4a4246..0fa29f4294 100644
--- a/pyrit/prompt_converter/math_prompt_converter.py
+++ b/pyrit/prompt_converter/math_prompt_converter.py
@@ -3,7 +3,6 @@
 
 import logging
 import pathlib
-from typing import Optional
 
 from pyrit.common.apply_defaults import REQUIRED_VALUE, apply_defaults
 from pyrit.common.path import CONVERTER_SEED_PROMPT_PATH
@@ -27,7 +26,7 @@ def __init__(
         self,
         *,
         converter_target: PromptTarget = REQUIRED_VALUE,  # type: ignore[ty:invalid-parameter-default]
-        prompt_template: Optional[SeedPrompt] = None,
+        prompt_template: SeedPrompt | None = None,
     ) -> None:
         """
         Initialize the converter with a specific target and template.
diff --git a/pyrit/prompt_converter/noise_converter.py b/pyrit/prompt_converter/noise_converter.py
index cfa4b83fd7..77e418e731 100644
--- a/pyrit/prompt_converter/noise_converter.py
+++ b/pyrit/prompt_converter/noise_converter.py
@@ -4,7 +4,6 @@
 import logging
 import pathlib
 import textwrap
-from typing import Optional
 
 from pyrit.common.apply_defaults import REQUIRED_VALUE, apply_defaults
 from pyrit.common.path import CONVERTER_SEED_PROMPT_PATH
@@ -27,9 +26,9 @@ def __init__(
         self,
         *,
         converter_target: PromptTarget = REQUIRED_VALUE,  # type: ignore[ty:invalid-parameter-default]
-        noise: Optional[str] = None,
+        noise: str | None = None,
         number_errors: int = 5,
-        prompt_template: Optional[SeedPrompt] = None,
+        prompt_template: SeedPrompt | None = None,
     ) -> None:
         """
         Initialize the converter with the specified parameters.
diff --git a/pyrit/prompt_converter/pdf_converter.py b/pyrit/prompt_converter/pdf_converter.py
index 4017f426e9..0e30a4d08f 100644
--- a/pyrit/prompt_converter/pdf_converter.py
+++ b/pyrit/prompt_converter/pdf_converter.py
@@ -5,7 +5,7 @@
 import hashlib
 from io import BytesIO
 from pathlib import Path
-from typing import Any, Optional
+from typing import Any
 
 from pypdf import PageObject, PdfReader, PdfWriter
 from reportlab.lib.units import mm
@@ -38,7 +38,7 @@ class PDFConverter(PromptConverter):
 
     def __init__(
         self,
-        prompt_template: Optional[SeedPrompt] = None,
+        prompt_template: SeedPrompt | None = None,
         font_type: str = "Helvetica",
         font_size: int = 12,
         font_color: tuple[int, int, int] = (255, 255, 255),
@@ -46,8 +46,8 @@ def __init__(
         page_height: int = 297,
         column_width: int = 0,
         row_height: int = 10,
-        existing_pdf: Optional[Path] = None,
-        injection_items: Optional[list[dict[str, Any]]] = None,
+        existing_pdf: Path | None = None,
+        injection_items: list[dict[str, Any]] | None = None,
     ) -> None:
         """
         Initialize the converter with the specified parameters.
@@ -78,9 +78,9 @@ def __init__(
         self._row_height = row_height
 
         # Keeping the user's path here
-        self._existing_pdf_path: Optional[Path] = existing_pdf
+        self._existing_pdf_path: Path | None = existing_pdf
         # We store the file data in a separate BytesIO for type checker compatibility
-        self._existing_pdf_bytes: Optional[BytesIO] = None
+        self._existing_pdf_bytes: BytesIO | None = None
 
         self._injection_items = injection_items or []
 
diff --git a/pyrit/prompt_converter/prompt_converter.py b/pyrit/prompt_converter/prompt_converter.py
index 0e6916f371..2f2375e1f2 100644
--- a/pyrit/prompt_converter/prompt_converter.py
+++ b/pyrit/prompt_converter/prompt_converter.py
@@ -6,7 +6,7 @@
 import inspect
 import re
 from dataclasses import dataclass
-from typing import TYPE_CHECKING, Any, ClassVar, Optional, Union, get_args
+from typing import TYPE_CHECKING, Any, ClassVar, Optional, get_args
 
 from pyrit import prompt_converter
 from pyrit.models import ComponentIdentifier, Identifiable, PromptDataType
@@ -56,7 +56,7 @@ class PromptConverter(Identifiable):
     #: ``super().__init__(converter_target=...)`` so the base class can validate it.
     TARGET_REQUIREMENTS: ClassVar[TargetRequirements] = TargetRequirements()
 
-    _identifier: Optional[ComponentIdentifier] = None
+    _identifier: ComponentIdentifier | None = None
 
     def __init_subclass__(cls, **kwargs: object) -> None:
         """
@@ -195,8 +195,8 @@ def _build_identifier(self) -> ComponentIdentifier:
     def _create_identifier(
         self,
         *,
-        params: Optional[dict[str, Any]] = None,
-        children: Optional[dict[str, Union[ComponentIdentifier, list[ComponentIdentifier]]]] = None,
+        params: dict[str, Any] | None = None,
+        children: dict[str, ComponentIdentifier | list[ComponentIdentifier]] | None = None,
     ) -> ComponentIdentifier:
         """
         Construct and return the converter identifier.
diff --git a/pyrit/prompt_converter/qr_code_converter.py b/pyrit/prompt_converter/qr_code_converter.py
index cc1424d14f..b77487b293 100644
--- a/pyrit/prompt_converter/qr_code_converter.py
+++ b/pyrit/prompt_converter/qr_code_converter.py
@@ -1,7 +1,6 @@
 # Copyright (c) Microsoft Corporation.
 # Licensed under the MIT license.
 
-from typing import Optional
 
 import segno
 
@@ -21,11 +20,11 @@ def __init__(
         border: int = 4,
         dark_color: tuple[int, int, int] = (0, 0, 0),
         light_color: tuple[int, int, int] = (255, 255, 255),
-        data_dark_color: Optional[tuple[int, int, int]] = None,
-        data_light_color: Optional[tuple[int, int, int]] = None,
-        finder_dark_color: Optional[tuple[int, int, int]] = None,
-        finder_light_color: Optional[tuple[int, int, int]] = None,
-        border_color: Optional[tuple[int, int, int]] = None,
+        data_dark_color: tuple[int, int, int] | None = None,
+        data_light_color: tuple[int, int, int] | None = None,
+        finder_dark_color: tuple[int, int, int] | None = None,
+        finder_light_color: tuple[int, int, int] | None = None,
+        border_color: tuple[int, int, int] | None = None,
     ) -> None:
         """
         Initialize the converter with specified parameters for QR code generation.
diff --git a/pyrit/prompt_converter/random_translation_converter.py b/pyrit/prompt_converter/random_translation_converter.py
index 769cb51611..239fc6c42c 100644
--- a/pyrit/prompt_converter/random_translation_converter.py
+++ b/pyrit/prompt_converter/random_translation_converter.py
@@ -4,7 +4,6 @@
 import logging
 import random
 from pathlib import Path
-from typing import Optional
 
 from pyrit.common.apply_defaults import REQUIRED_VALUE, apply_defaults
 from pyrit.common.path import CONVERTER_SEED_PROMPT_PATH, DATASETS_PATH
@@ -36,9 +35,9 @@ def __init__(
         self,
         *,
         converter_target: PromptTarget = REQUIRED_VALUE,  # type: ignore[ty:invalid-parameter-default]
-        system_prompt_template: Optional[SeedPrompt] = None,
-        languages: Optional[list[str]] = None,
-        word_selection_strategy: Optional[WordSelectionStrategy] = None,
+        system_prompt_template: SeedPrompt | None = None,
+        languages: list[str] | None = None,
+        word_selection_strategy: WordSelectionStrategy | None = None,
     ) -> None:
         """
         Initialize the converter with a target, an optional system prompt template, and language options.
diff --git a/pyrit/prompt_converter/repeat_token_converter.py b/pyrit/prompt_converter/repeat_token_converter.py
index c2b5a74825..c711448ca4 100644
--- a/pyrit/prompt_converter/repeat_token_converter.py
+++ b/pyrit/prompt_converter/repeat_token_converter.py
@@ -2,7 +2,7 @@
 # Licensed under the MIT license.
 
 import re
-from typing import Literal, Optional
+from typing import Literal
 
 from pyrit.models import ComponentIdentifier, PromptDataType
 from pyrit.prompt_converter.prompt_converter import ConverterResult, PromptConverter
@@ -35,7 +35,7 @@ def __init__(
         *,
         token_to_repeat: str,
         times_to_repeat: int,
-        token_insert_mode: Optional[Literal["split", "prepend", "append", "repeat"]] = None,
+        token_insert_mode: Literal["split", "prepend", "append", "repeat"] | None = None,
     ) -> None:
         """
         Initialize the converter with the specified token, number of repetitions, and insertion mode.
diff --git a/pyrit/prompt_converter/scientific_translation_converter.py b/pyrit/prompt_converter/scientific_translation_converter.py
index 85e05428fa..b4229a5226 100644
--- a/pyrit/prompt_converter/scientific_translation_converter.py
+++ b/pyrit/prompt_converter/scientific_translation_converter.py
@@ -3,7 +3,7 @@
 
 import logging
 import pathlib
-from typing import Literal, Optional, get_args
+from typing import Literal, get_args
 
 from pyrit.common.apply_defaults import REQUIRED_VALUE, apply_defaults
 from pyrit.common.path import CONVERTER_SEED_PROMPT_PATH
@@ -46,7 +46,7 @@ def __init__(
         *,
         converter_target: PromptTarget = REQUIRED_VALUE,  # type: ignore[ty:invalid-parameter-default]
         mode: str = "combined",
-        prompt_template: Optional[SeedPrompt] = None,
+        prompt_template: SeedPrompt | None = None,
     ) -> None:
         """
         Initialize the scientific translation converter.
diff --git a/pyrit/prompt_converter/string_join_converter.py b/pyrit/prompt_converter/string_join_converter.py
index cd961fd65f..e927e144b6 100644
--- a/pyrit/prompt_converter/string_join_converter.py
+++ b/pyrit/prompt_converter/string_join_converter.py
@@ -1,7 +1,6 @@
 # Copyright (c) Microsoft Corporation.
 # Licensed under the MIT license.
 
-from typing import Optional
 
 from pyrit.models import ComponentIdentifier
 from pyrit.prompt_converter.text_selection_strategy import WordSelectionStrategy
@@ -17,7 +16,7 @@ def __init__(
         self,
         *,
         join_value: str = "-",
-        word_selection_strategy: Optional[WordSelectionStrategy] = None,
+        word_selection_strategy: WordSelectionStrategy | None = None,
     ) -> None:
         """
         Initialize the converter with the specified join value and selection strategy.
diff --git a/pyrit/prompt_converter/template_segment_converter.py b/pyrit/prompt_converter/template_segment_converter.py
index ed21b0434e..b9bafbce34 100644
--- a/pyrit/prompt_converter/template_segment_converter.py
+++ b/pyrit/prompt_converter/template_segment_converter.py
@@ -5,7 +5,6 @@
 import logging
 import pathlib
 import random
-from typing import Optional
 
 from pyrit.common.path import CONVERTER_SEED_PROMPT_PATH
 from pyrit.models import ComponentIdentifier, PromptDataType, SeedPrompt
@@ -28,7 +27,7 @@ class TemplateSegmentConverter(PromptConverter):
     def __init__(
         self,
         *,
-        prompt_template: Optional[SeedPrompt] = None,
+        prompt_template: SeedPrompt | None = None,
     ) -> None:
         """
         Initialize the converter with the specified target and prompt template.
diff --git a/pyrit/prompt_converter/tense_converter.py b/pyrit/prompt_converter/tense_converter.py
index f8f20468d6..8f0852b2c2 100644
--- a/pyrit/prompt_converter/tense_converter.py
+++ b/pyrit/prompt_converter/tense_converter.py
@@ -3,7 +3,6 @@
 
 import logging
 import pathlib
-from typing import Optional
 
 from pyrit.common.apply_defaults import REQUIRED_VALUE, apply_defaults
 from pyrit.common.path import CONVERTER_SEED_PROMPT_PATH
@@ -27,7 +26,7 @@ def __init__(
         *,
         converter_target: PromptTarget = REQUIRED_VALUE,  # type: ignore[ty:invalid-parameter-default]
         tense: str,
-        prompt_template: Optional[SeedPrompt] = None,
+        prompt_template: SeedPrompt | None = None,
     ) -> None:
         """
         Initialize the converter with the target chat support, tense, and optional prompt template.
diff --git a/pyrit/prompt_converter/text_selection_strategy.py b/pyrit/prompt_converter/text_selection_strategy.py
index 6dbc8a8b63..641ad27d96 100644
--- a/pyrit/prompt_converter/text_selection_strategy.py
+++ b/pyrit/prompt_converter/text_selection_strategy.py
@@ -5,7 +5,6 @@
 import random
 import re
 from re import Pattern
-from typing import Optional, Union
 
 
 class TextSelectionStrategy(abc.ABC):
@@ -133,7 +132,7 @@ class IndexSelectionStrategy(TextSelectionStrategy):
     Selects text based on absolute character indices.
     """
 
-    def __init__(self, *, start: int = 0, end: Optional[int] = None) -> None:
+    def __init__(self, *, start: int = 0, end: int | None = None) -> None:
         """
         Initialize the index selection strategy.
 
@@ -165,7 +164,7 @@ class RegexSelectionStrategy(TextSelectionStrategy):
     Selects text based on the first regex match.
     """
 
-    def __init__(self, *, pattern: Union[str, Pattern[str]]) -> None:
+    def __init__(self, *, pattern: str | Pattern[str]) -> None:
         """
         Initialize the regex selection strategy.
 
@@ -290,7 +289,7 @@ class ProportionSelectionStrategy(TextSelectionStrategy):
     Selects a proportion of text anchored to a specific position (start, end, middle, or random).
     """
 
-    def __init__(self, *, proportion: float, anchor: str = "start", seed: Optional[int] = None) -> None:
+    def __init__(self, *, proportion: float, anchor: str = "start", seed: int | None = None) -> None:
         """
         Initialize the proportion selection strategy.
 
@@ -473,7 +472,7 @@ class WordProportionSelectionStrategy(WordSelectionStrategy):
     Selects a random proportion of words.
     """
 
-    def __init__(self, *, proportion: float, seed: Optional[int] = None) -> None:
+    def __init__(self, *, proportion: float, seed: int | None = None) -> None:
         """
         Initialize the word proportion selection strategy.
 
@@ -515,7 +514,7 @@ class WordRegexSelectionStrategy(WordSelectionStrategy):
     Selects words that match a regex pattern.
     """
 
-    def __init__(self, *, pattern: Union[str, Pattern[str]]) -> None:
+    def __init__(self, *, pattern: str | Pattern[str]) -> None:
         """
         Initialize the word regex selection strategy.
 
diff --git a/pyrit/prompt_converter/token_smuggling/sneaky_bits_smuggler_converter.py b/pyrit/prompt_converter/token_smuggling/sneaky_bits_smuggler_converter.py
index 503c9dab9b..c4fc1bbaec 100644
--- a/pyrit/prompt_converter/token_smuggling/sneaky_bits_smuggler_converter.py
+++ b/pyrit/prompt_converter/token_smuggling/sneaky_bits_smuggler_converter.py
@@ -2,7 +2,7 @@
 # Licensed under the MIT license.
 
 import logging
-from typing import Literal, Optional
+from typing import Literal
 
 from pyrit.models import ComponentIdentifier
 from pyrit.prompt_converter.token_smuggling.base import SmugglerConverter
@@ -25,8 +25,8 @@ class SneakyBitsSmugglerConverter(SmugglerConverter):
     def __init__(
         self,
         action: Literal["encode", "decode"] = "encode",
-        zero_char: Optional[str] = None,
-        one_char: Optional[str] = None,
+        zero_char: str | None = None,
+        one_char: str | None = None,
     ) -> None:
         """
         Initialize the converter with options for encoding/decoding in Sneaky Bits mode.
diff --git a/pyrit/prompt_converter/token_smuggling/variation_selector_smuggler_converter.py b/pyrit/prompt_converter/token_smuggling/variation_selector_smuggler_converter.py
index f70ee4902b..077c91db84 100644
--- a/pyrit/prompt_converter/token_smuggling/variation_selector_smuggler_converter.py
+++ b/pyrit/prompt_converter/token_smuggling/variation_selector_smuggler_converter.py
@@ -2,7 +2,7 @@
 # Licensed under the MIT license.
 
 import logging
-from typing import Literal, Optional
+from typing import Literal
 
 from pyrit.models import ComponentIdentifier
 from pyrit.prompt_converter.token_smuggling.base import SmugglerConverter
@@ -32,7 +32,7 @@ class VariationSelectorSmugglerConverter(SmugglerConverter):
     def __init__(
         self,
         action: Literal["encode", "decode"] = "encode",
-        base_char_utf8: Optional[str] = None,
+        base_char_utf8: str | None = None,
         embed_in_base: bool = True,
     ) -> None:
         """
diff --git a/pyrit/prompt_converter/tone_converter.py b/pyrit/prompt_converter/tone_converter.py
index c21a118603..562a4ee6af 100644
--- a/pyrit/prompt_converter/tone_converter.py
+++ b/pyrit/prompt_converter/tone_converter.py
@@ -3,7 +3,6 @@
 
 import logging
 import pathlib
-from typing import Optional
 
 from pyrit.common.apply_defaults import REQUIRED_VALUE, apply_defaults
 from pyrit.common.path import CONVERTER_SEED_PROMPT_PATH
@@ -27,7 +26,7 @@ def __init__(
         *,
         converter_target: PromptTarget = REQUIRED_VALUE,  # type: ignore[ty:invalid-parameter-default]
         tone: str,
-        prompt_template: Optional[SeedPrompt] = None,
+        prompt_template: SeedPrompt | None = None,
     ) -> None:
         """
         Initialize the converter with the target chat support, tone, and optional prompt template.
diff --git a/pyrit/prompt_converter/toxic_sentence_generator_converter.py b/pyrit/prompt_converter/toxic_sentence_generator_converter.py
index 3159cf1de7..07cfc3744e 100644
--- a/pyrit/prompt_converter/toxic_sentence_generator_converter.py
+++ b/pyrit/prompt_converter/toxic_sentence_generator_converter.py
@@ -7,7 +7,6 @@
 
 import logging
 import pathlib
-from typing import Optional
 
 from pyrit.common.apply_defaults import REQUIRED_VALUE, apply_defaults
 from pyrit.common.path import CONVERTER_SEED_PROMPT_PATH
@@ -35,7 +34,7 @@ def __init__(
         self,
         *,
         converter_target: PromptTarget = REQUIRED_VALUE,  # type: ignore[ty:invalid-parameter-default]
-        prompt_template: Optional[SeedPrompt] = None,
+        prompt_template: SeedPrompt | None = None,
     ) -> None:
         """
         Initialize the converter with a specific target and template.
diff --git a/pyrit/prompt_converter/unicode_replacement_converter.py b/pyrit/prompt_converter/unicode_replacement_converter.py
index 71a0e52e54..150499ab72 100644
--- a/pyrit/prompt_converter/unicode_replacement_converter.py
+++ b/pyrit/prompt_converter/unicode_replacement_converter.py
@@ -1,7 +1,6 @@
 # Copyright (c) Microsoft Corporation.
 # Licensed under the MIT license.
 
-from typing import Optional
 
 from pyrit.models import ComponentIdentifier
 from pyrit.prompt_converter.text_selection_strategy import WordSelectionStrategy
@@ -17,7 +16,7 @@ def __init__(
         self,
         *,
         encode_spaces: bool = False,
-        word_selection_strategy: Optional[WordSelectionStrategy] = None,
+        word_selection_strategy: WordSelectionStrategy | None = None,
     ) -> None:
         """
         Initialize the converter with the specified selection strategy.
diff --git a/pyrit/prompt_converter/word_doc_converter.py b/pyrit/prompt_converter/word_doc_converter.py
index 1dc5d00b5c..b811ab1b3f 100644
--- a/pyrit/prompt_converter/word_doc_converter.py
+++ b/pyrit/prompt_converter/word_doc_converter.py
@@ -7,7 +7,7 @@
 import hashlib
 from dataclasses import dataclass
 from io import BytesIO
-from typing import TYPE_CHECKING, Any, Optional
+from typing import TYPE_CHECKING, Any
 
 from docx import Document
 
@@ -26,7 +26,7 @@
 class _WordDocInjectionConfig:
     """Configuration for how to inject content into a Word document."""
 
-    existing_docx: Optional[Path]
+    existing_docx: Path | None
     placeholder: str
 
 
@@ -66,8 +66,8 @@ class WordDocConverter(PromptConverter):
     def __init__(
         self,
         *,
-        prompt_template: Optional[SeedPrompt] = None,
-        existing_docx: Optional[Path] = None,
+        prompt_template: SeedPrompt | None = None,
+        existing_docx: Path | None = None,
         placeholder: str = "{{INJECTION_PLACEHOLDER}}",
     ) -> None:
         """
@@ -112,7 +112,7 @@ def _build_identifier(self) -> ComponentIdentifier:
         Returns:
             ComponentIdentifier: The identifier with converter-specific parameters.
         """
-        template_hash: Optional[str] = None
+        template_hash: str | None = None
         if self._prompt_template:
             template_hash = hashlib.sha256(str(self._prompt_template.value).encode("utf-8")).hexdigest()[:16]
 
diff --git a/pyrit/prompt_converter/word_level_converter.py b/pyrit/prompt_converter/word_level_converter.py
index 5a2f874f0c..2ca186014a 100644
--- a/pyrit/prompt_converter/word_level_converter.py
+++ b/pyrit/prompt_converter/word_level_converter.py
@@ -2,7 +2,7 @@
 # Licensed under the MIT license.
 
 import abc
-from typing import Any, Optional
+from typing import Any
 
 from pyrit.models import ComponentIdentifier, PromptDataType
 from pyrit.prompt_converter.prompt_converter import ConverterResult, PromptConverter
@@ -30,8 +30,8 @@ class WordLevelConverter(PromptConverter):
     def __init__(
         self,
         *,
-        word_selection_strategy: Optional[WordSelectionStrategy] = None,
-        word_split_separator: Optional[str] = " ",
+        word_selection_strategy: WordSelectionStrategy | None = None,
+        word_split_separator: str | None = " ",
         **kwargs: Any,
     ) -> None:
         """
diff --git a/pyrit/prompt_converter/zalgo_converter.py b/pyrit/prompt_converter/zalgo_converter.py
index ddd7c686ec..4da331cf79 100644
--- a/pyrit/prompt_converter/zalgo_converter.py
+++ b/pyrit/prompt_converter/zalgo_converter.py
@@ -3,7 +3,6 @@
 
 import logging
 import random
-from typing import Optional
 
 from pyrit.models import ComponentIdentifier
 from pyrit.prompt_converter.text_selection_strategy import WordSelectionStrategy
@@ -25,8 +24,8 @@ def __init__(
         self,
         *,
         intensity: int = 10,
-        seed: Optional[int] = None,
-        word_selection_strategy: Optional[WordSelectionStrategy] = None,
+        seed: int | None = None,
+        word_selection_strategy: WordSelectionStrategy | None = None,
     ) -> None:
         """
         Initialize the converter with the specified selection parameters.
diff --git a/pyrit/prompt_normalizer/normalizer_request.py b/pyrit/prompt_normalizer/normalizer_request.py
index c030ca5278..e553fe8637 100644
--- a/pyrit/prompt_normalizer/normalizer_request.py
+++ b/pyrit/prompt_normalizer/normalizer_request.py
@@ -2,7 +2,6 @@
 # Licensed under the MIT license.
 
 from dataclasses import dataclass
-from typing import Optional
 
 from pyrit.models import Message
 from pyrit.prompt_normalizer.prompt_converter_configuration import (
@@ -27,7 +26,7 @@ def __init__(
         message: Message,
         request_converter_configurations: list[PromptConverterConfiguration] | None = None,
         response_converter_configurations: list[PromptConverterConfiguration] | None = None,
-        conversation_id: Optional[str] = None,
+        conversation_id: str | None = None,
     ) -> None:
         """
         Initialize a normalizer request.
diff --git a/pyrit/prompt_normalizer/prompt_converter_configuration.py b/pyrit/prompt_normalizer/prompt_converter_configuration.py
index cb9ae55425..3ba455af64 100644
--- a/pyrit/prompt_normalizer/prompt_converter_configuration.py
+++ b/pyrit/prompt_normalizer/prompt_converter_configuration.py
@@ -2,7 +2,6 @@
 # Licensed under the MIT license.
 
 from dataclasses import dataclass
-from typing import Optional
 
 from pyrit.models import PromptDataType
 from pyrit.prompt_converter import PromptConverter
@@ -19,8 +18,8 @@ class PromptConverterConfiguration:
     """
 
     converters: list[PromptConverter]
-    indexes_to_apply: Optional[list[int]] = None
-    prompt_data_types_to_apply: Optional[list[PromptDataType]] = None
+    indexes_to_apply: list[int] | None = None
+    prompt_data_types_to_apply: list[PromptDataType] | None = None
 
     @classmethod
     def from_converters(cls, *, converters: list[PromptConverter]) -> list["PromptConverterConfiguration"]:
diff --git a/pyrit/prompt_normalizer/prompt_normalizer.py b/pyrit/prompt_normalizer/prompt_normalizer.py
index 9c23f91cf3..95196db642 100644
--- a/pyrit/prompt_normalizer/prompt_normalizer.py
+++ b/pyrit/prompt_normalizer/prompt_normalizer.py
@@ -9,7 +9,7 @@
 import traceback
 import wave
 from pathlib import Path
-from typing import Any, Optional
+from typing import Any
 from uuid import uuid4
 
 from pyrit.common.deprecation import print_deprecation_message
@@ -68,11 +68,11 @@ async def send_prompt_async(
         *,
         message: Message,
         target: PromptTarget,
-        conversation_id: Optional[str] = None,
+        conversation_id: str | None = None,
         request_converter_configurations: list[PromptConverterConfiguration] | None = None,
         response_converter_configurations: list[PromptConverterConfiguration] | None = None,
-        labels: Optional[dict[str, str]] = None,
-        attack_identifier: Optional[ComponentIdentifier] = None,
+        labels: dict[str, str] | None = None,
+        attack_identifier: ComponentIdentifier | None = None,
     ) -> Message:
         """
         Send a single request to a target.
@@ -196,8 +196,8 @@ async def send_prompt_batch_to_target_async(
         *,
         requests: list[NormalizerRequest],
         target: PromptTarget,
-        labels: Optional[dict[str, str]] = None,
-        attack_identifier: Optional[ComponentIdentifier] = None,
+        labels: dict[str, str] | None = None,
+        attack_identifier: ComponentIdentifier | None = None,
         batch_size: int = 10,
     ) -> list[Message]:
         """
@@ -397,10 +397,10 @@ async def add_prepended_conversation_to_memory_async(
         self,
         conversation_id: str,
         should_convert: bool = True,
-        converter_configurations: Optional[list[PromptConverterConfiguration]] = None,
-        attack_identifier: Optional[ComponentIdentifier] = None,
-        prepended_conversation: Optional[list[Message]] = None,
-    ) -> Optional[list[Message]]:
+        converter_configurations: list[PromptConverterConfiguration] | None = None,
+        attack_identifier: ComponentIdentifier | None = None,
+        prepended_conversation: list[Message] | None = None,
+    ) -> list[Message] | None:
         """
         Process the prepended conversation by converting it if needed and adding it to memory.
 
@@ -454,10 +454,10 @@ async def add_prepended_conversation_to_memory(  # pyrit-async-suffix-exempt
         self,
         conversation_id: str,
         should_convert: bool = True,
-        converter_configurations: Optional[list[PromptConverterConfiguration]] = None,
-        attack_identifier: Optional[ComponentIdentifier] = None,
-        prepended_conversation: Optional[list[Message]] = None,
-    ) -> Optional[list[Message]]:
+        converter_configurations: list[PromptConverterConfiguration] | None = None,
+        attack_identifier: ComponentIdentifier | None = None,
+        prepended_conversation: list[Message] | None = None,
+    ) -> list[Message] | None:
         """
         Use ``add_prepended_conversation_to_memory_async`` instead; this is a deprecated alias.
 
diff --git a/pyrit/prompt_target/azure_blob_storage_target.py b/pyrit/prompt_target/azure_blob_storage_target.py
index 184cb1664e..b3b10a04e2 100644
--- a/pyrit/prompt_target/azure_blob_storage_target.py
+++ b/pyrit/prompt_target/azure_blob_storage_target.py
@@ -3,7 +3,6 @@
 
 import logging
 from enum import Enum
-from typing import Optional
 from urllib.parse import urlparse
 
 from azure.core.exceptions import ClientAuthenticationError
@@ -69,11 +68,11 @@ class AzureBlobStorageTarget(PromptTarget):
     def __init__(
         self,
         *,
-        container_url: Optional[str] = None,
-        sas_token: Optional[str] = None,
+        container_url: str | None = None,
+        sas_token: str | None = None,
         blob_content_type: SupportedContentType = SupportedContentType.PLAIN_TEXT,
-        max_requests_per_minute: Optional[int] = None,
-        custom_configuration: Optional[TargetConfiguration] = None,
+        max_requests_per_minute: int | None = None,
+        custom_configuration: TargetConfiguration | None = None,
     ) -> None:
         """
         Initialize the Azure Blob Storage target.
@@ -95,8 +94,8 @@ def __init__(
             env_var_name=self.AZURE_STORAGE_CONTAINER_ENVIRONMENT_VARIABLE, passed_value=container_url
         )
 
-        self._sas_token: Optional[str] = sas_token
-        self._client_async: Optional[AsyncContainerClient] = None
+        self._sas_token: str | None = sas_token
+        self._client_async: AsyncContainerClient | None = None
 
         super().__init__(
             endpoint=self._container_url,
diff --git a/pyrit/prompt_target/batch_helper.py b/pyrit/prompt_target/batch_helper.py
index 95ec6809fb..399465e4fb 100644
--- a/pyrit/prompt_target/batch_helper.py
+++ b/pyrit/prompt_target/batch_helper.py
@@ -3,7 +3,7 @@
 
 import asyncio
 from collections.abc import Callable, Generator, Sequence
-from typing import Any, Optional
+from typing import Any
 
 from pyrit.prompt_target.common.prompt_target import PromptTarget
 
@@ -31,7 +31,7 @@ def _get_chunks(*args: Sequence[Any], batch_size: int) -> Generator[list[Sequenc
         yield [arg[i : i + batch_size] for arg in args]
 
 
-def _validate_rate_limit_parameters(prompt_target: Optional[PromptTarget], batch_size: int) -> None:
+def _validate_rate_limit_parameters(prompt_target: PromptTarget | None, batch_size: int) -> None:
     """
     Validate the constraints between Rate Limit (Requests Per Minute) and batch size.
 
@@ -49,7 +49,7 @@ def _validate_rate_limit_parameters(prompt_target: Optional[PromptTarget], batch
 
 async def batch_task_async(
     *,
-    prompt_target: Optional[PromptTarget] = None,
+    prompt_target: PromptTarget | None = None,
     batch_size: int,
     items_to_batch: Sequence[Sequence[Any]],
     task_func: Callable[..., Any],
diff --git a/pyrit/prompt_target/common/prompt_target.py b/pyrit/prompt_target/common/prompt_target.py
index aa13658aac..4c6c81fa3c 100644
--- a/pyrit/prompt_target/common/prompt_target.py
+++ b/pyrit/prompt_target/common/prompt_target.py
@@ -3,7 +3,7 @@
 
 import abc
 import logging
-from typing import Any, Union, final
+from typing import Any, final
 
 from pyrit.common.deprecation import print_deprecation_message
 from pyrit.memory import CentralMemory, MemoryInterface
@@ -319,7 +319,7 @@ def _create_identifier(
         self,
         *,
         params: dict[str, Any] | None = None,
-        children: dict[str, Union[ComponentIdentifier, list[ComponentIdentifier]]] | None = None,
+        children: dict[str, ComponentIdentifier | list[ComponentIdentifier]] | None = None,
     ) -> ComponentIdentifier:
         """
         Construct the target identifier.
diff --git a/pyrit/prompt_target/common/target_capabilities.py b/pyrit/prompt_target/common/target_capabilities.py
index 7f1010745f..719c441d38 100644
--- a/pyrit/prompt_target/common/target_capabilities.py
+++ b/pyrit/prompt_target/common/target_capabilities.py
@@ -5,7 +5,7 @@
 from dataclasses import dataclass, field
 from enum import Enum
 from types import MappingProxyType
-from typing import NoReturn, Optional, cast
+from typing import NoReturn, cast
 
 from pyrit.models import PromptDataType
 
@@ -165,7 +165,7 @@ def includes(self, *, capability: CapabilityName) -> bool:
         return bool(getattr(self, capability.value))
 
     @staticmethod
-    def get_known_capabilities(underlying_model: str) -> "Optional[TargetCapabilities]":
+    def get_known_capabilities(underlying_model: str) -> "TargetCapabilities | None":
         """
         Return the known capabilities for a specific underlying model, or None if unrecognized.
 
diff --git a/pyrit/prompt_target/common/utils.py b/pyrit/prompt_target/common/utils.py
index 2aaa10bb68..6b6a74a813 100644
--- a/pyrit/prompt_target/common/utils.py
+++ b/pyrit/prompt_target/common/utils.py
@@ -3,12 +3,12 @@
 
 import asyncio
 from collections.abc import Callable
-from typing import Any, Optional
+from typing import Any
 
 from pyrit.exceptions import PyritException
 
 
-def validate_temperature(temperature: Optional[float]) -> None:
+def validate_temperature(temperature: float | None) -> None:
     """
     Validate that temperature parameter is within valid range.
 
@@ -22,7 +22,7 @@ def validate_temperature(temperature: Optional[float]) -> None:
         raise PyritException(message="temperature must be between 0 and 2 (inclusive).")
 
 
-def validate_top_p(top_p: Optional[float]) -> None:
+def validate_top_p(top_p: float | None) -> None:
     """
     Validate that top_p parameter is within valid range.
 
diff --git a/pyrit/prompt_target/gandalf_target.py b/pyrit/prompt_target/gandalf_target.py
index 1bad549c7f..b2dc6e342a 100644
--- a/pyrit/prompt_target/gandalf_target.py
+++ b/pyrit/prompt_target/gandalf_target.py
@@ -4,7 +4,6 @@
 import enum
 import json
 import logging
-from typing import Optional
 
 from pyrit.common import net_utility
 from pyrit.common.deprecation import print_deprecation_message
@@ -43,8 +42,8 @@ def __init__(
         self,
         *,
         level: GandalfLevel,
-        max_requests_per_minute: Optional[int] = None,
-        custom_configuration: Optional[TargetConfiguration] = None,
+        max_requests_per_minute: int | None = None,
+        custom_configuration: TargetConfiguration | None = None,
     ) -> None:
         """
         Initialize the Gandalf target.
diff --git a/pyrit/prompt_target/http_target/http_target.py b/pyrit/prompt_target/http_target/http_target.py
index 6ed37c0da3..ce3028ca89 100644
--- a/pyrit/prompt_target/http_target/http_target.py
+++ b/pyrit/prompt_target/http_target/http_target.py
@@ -6,7 +6,7 @@
 import logging
 import re
 from collections.abc import Callable
-from typing import Any, Optional
+from typing import Any
 
 import httpx
 
@@ -37,11 +37,11 @@ def __init__(
         http_request: str,
         prompt_regex_string: str = "{PROMPT}",
         use_tls: bool = True,
-        callback_function: Optional[Callable[..., Any]] = None,
-        max_requests_per_minute: Optional[int] = None,
-        client: Optional[httpx.AsyncClient] = None,
+        callback_function: Callable[..., Any] | None = None,
+        max_requests_per_minute: int | None = None,
+        client: httpx.AsyncClient | None = None,
         model_name: str = "",
-        custom_configuration: Optional[TargetConfiguration] = None,
+        custom_configuration: TargetConfiguration | None = None,
         **httpx_client_kwargs: Any,
     ) -> None:
         """
@@ -108,7 +108,7 @@ def with_client(
         http_request: str,
         prompt_regex_string: str = "{PROMPT}",
         callback_function: Callable[..., Any] | None = None,
-        max_requests_per_minute: Optional[int] = None,
+        max_requests_per_minute: int | None = None,
     ) -> "HTTPTarget":
         """
         Alternative constructor that accepts a pre-configured httpx client.
diff --git a/pyrit/prompt_target/http_target/http_target_callback_functions.py b/pyrit/prompt_target/http_target/http_target_callback_functions.py
index 90cc7f79a3..8d749af73d 100644
--- a/pyrit/prompt_target/http_target/http_target_callback_functions.py
+++ b/pyrit/prompt_target/http_target/http_target_callback_functions.py
@@ -5,7 +5,7 @@
 import json
 import re
 from collections.abc import Callable
-from typing import Any, Optional
+from typing import Any
 
 import requests
 
@@ -42,7 +42,7 @@ def parse_json_http_response(response: requests.Response) -> str:
 
 
 def get_http_target_regex_matching_callback_function(
-    key: str, url: Optional[str] = None
+    key: str, url: str | None = None
 ) -> Callable[[requests.Response], str]:
     """
     Get a callback function that parses HTTP responses using regex matching.
diff --git a/pyrit/prompt_target/http_target/httpx_api_target.py b/pyrit/prompt_target/http_target/httpx_api_target.py
index bd32fd1fe2..95f0c47124 100644
--- a/pyrit/prompt_target/http_target/httpx_api_target.py
+++ b/pyrit/prompt_target/http_target/httpx_api_target.py
@@ -5,7 +5,7 @@
 import mimetypes
 from collections.abc import Callable
 from pathlib import Path
-from typing import Any, Literal, Optional
+from typing import Any, Literal
 
 import aiofiles
 import httpx
@@ -42,15 +42,15 @@ def __init__(
         *,
         http_url: str,
         method: Literal["GET", "POST", "PUT", "DELETE", "PATCH", "HEAD", "OPTIONS"] = "POST",
-        file_path: Optional[str] = None,
-        json_data: Optional[dict[str, Any]] = None,
-        form_data: Optional[dict[str, Any]] = None,
-        params: Optional[dict[str, Any]] = None,
-        headers: Optional[dict[str, str]] = None,
-        http2: Optional[bool] = None,
+        file_path: str | None = None,
+        json_data: dict[str, Any] | None = None,
+        form_data: dict[str, Any] | None = None,
+        params: dict[str, Any] | None = None,
+        headers: dict[str, str] | None = None,
+        http2: bool | None = None,
         callback_function: Callable[..., Any] | None = None,
-        max_requests_per_minute: Optional[int] = None,
-        custom_configuration: Optional[TargetConfiguration] = None,
+        max_requests_per_minute: int | None = None,
+        custom_configuration: TargetConfiguration | None = None,
         **httpx_client_kwargs: Any,
     ) -> None:
         """
diff --git a/pyrit/prompt_target/openai/openai_chat_target.py b/pyrit/prompt_target/openai/openai_chat_target.py
index f82fc40e29..1fd2400ca9 100644
--- a/pyrit/prompt_target/openai/openai_chat_target.py
+++ b/pyrit/prompt_target/openai/openai_chat_target.py
@@ -5,7 +5,7 @@
 import json
 import logging
 from collections.abc import MutableSequence
-from typing import Any, Optional
+from typing import Any
 
 from pyrit.common.data_url_converter import convert_local_image_to_data_url_async
 from pyrit.exceptions import (
@@ -80,17 +80,17 @@ class OpenAIChatTarget(OpenAITarget):
     def __init__(
         self,
         *,
-        max_completion_tokens: Optional[int] = None,
-        max_tokens: Optional[int] = None,
-        temperature: Optional[float] = None,
-        top_p: Optional[float] = None,
-        frequency_penalty: Optional[float] = None,
-        presence_penalty: Optional[float] = None,
-        seed: Optional[int] = None,
-        n: Optional[int] = None,
-        audio_response_config: Optional[OpenAIChatAudioConfig] = None,
-        extra_body_parameters: Optional[dict[str, Any]] = None,
-        custom_configuration: Optional[TargetConfiguration] = None,
+        max_completion_tokens: int | None = None,
+        max_tokens: int | None = None,
+        temperature: float | None = None,
+        top_p: float | None = None,
+        frequency_penalty: float | None = None,
+        presence_penalty: float | None = None,
+        seed: int | None = None,
+        n: int | None = None,
+        audio_response_config: OpenAIChatAudioConfig | None = None,
+        extra_body_parameters: dict[str, Any] | None = None,
+        custom_configuration: TargetConfiguration | None = None,
         **kwargs: Any,
     ) -> None:
         """
@@ -259,7 +259,7 @@ def _check_content_filter(self, response: Any) -> bool:
             pass
         return False
 
-    def _extract_partial_content(self, response: Any) -> Optional[str]:
+    def _extract_partial_content(self, response: Any) -> str | None:
         """
         Extract partial content from a Chat Completions response with finish_reason=content_filter.
 
@@ -279,7 +279,7 @@ def _extract_partial_content(self, response: Any) -> Optional[str]:
             pass
         return None
 
-    def _validate_response(self, response: Any, request: MessagePiece) -> Optional[Message]:
+    def _validate_response(self, response: Any, request: MessagePiece) -> Message | None:
         """
         Validate a Chat Completions API response for errors.
 
@@ -415,7 +415,7 @@ async def _construct_message_from_response_async(self, response: Any, request: M
             audio_response = message.audio
 
             # Add transcript as text piece with metadata
-            audio_transcript: Optional[str] = getattr(audio_response, "transcript", None)
+            audio_transcript: str | None = getattr(audio_response, "transcript", None)
             if audio_transcript:
                 transcript_piece = construct_response_from_request(
                     request=request,
@@ -426,7 +426,7 @@ async def _construct_message_from_response_async(self, response: Any, request: M
                 pieces.append(transcript_piece)
 
             # Save audio data and add as audio_path piece
-            audio_data: Optional[str] = getattr(audio_response, "data", None)
+            audio_data: str | None = getattr(audio_response, "data", None)
             if audio_data:
                 audio_path = await self._save_audio_response_async(audio_data_base64=audio_data)
                 audio_piece = construct_response_from_request(
@@ -676,7 +676,7 @@ async def _construct_request_body_async(
         # Filter out None values
         return {k: v for k, v in body_parameters.items() if v is not None}
 
-    def _build_response_format(self, json_config: _JsonResponseConfig) -> Optional[dict[str, Any]]:
+    def _build_response_format(self, json_config: _JsonResponseConfig) -> dict[str, Any] | None:
         if not json_config.enabled:
             return None
 
diff --git a/pyrit/prompt_target/openai/openai_completion_target.py b/pyrit/prompt_target/openai/openai_completion_target.py
index 0f43ac5af8..4c4ff810c3 100644
--- a/pyrit/prompt_target/openai/openai_completion_target.py
+++ b/pyrit/prompt_target/openai/openai_completion_target.py
@@ -2,7 +2,7 @@
 # Licensed under the MIT license.
 
 import logging
-from typing import Any, Optional
+from typing import Any
 
 from pyrit.exceptions.exception_classes import (
     pyrit_target_retry,
@@ -23,13 +23,13 @@ class OpenAICompletionTarget(OpenAITarget):
 
     def __init__(
         self,
-        max_tokens: Optional[int] = None,
-        temperature: Optional[float] = None,
-        top_p: Optional[float] = None,
-        presence_penalty: Optional[float] = None,
-        frequency_penalty: Optional[float] = None,
-        n: Optional[int] = None,
-        custom_configuration: Optional[TargetConfiguration] = None,
+        max_tokens: int | None = None,
+        temperature: float | None = None,
+        top_p: float | None = None,
+        presence_penalty: float | None = None,
+        frequency_penalty: float | None = None,
+        n: int | None = None,
+        custom_configuration: TargetConfiguration | None = None,
         *args: Any,
         **kwargs: Any,
     ) -> None:
diff --git a/pyrit/prompt_target/openai/openai_error_handling.py b/pyrit/prompt_target/openai/openai_error_handling.py
index bc0daa77ae..3848675794 100644
--- a/pyrit/prompt_target/openai/openai_error_handling.py
+++ b/pyrit/prompt_target/openai/openai_error_handling.py
@@ -10,12 +10,11 @@
 
 import json
 import logging
-from typing import Optional, Union
 
 logger = logging.getLogger(__name__)
 
 
-def _extract_request_id_from_exception(exc: Exception) -> Optional[str]:
+def _extract_request_id_from_exception(exc: Exception) -> str | None:
     """
     Extract the x-request-id from an OpenAI SDK exception for logging/telemetry.
 
@@ -36,7 +35,7 @@ def _extract_request_id_from_exception(exc: Exception) -> Optional[str]:
     return None
 
 
-def _extract_retry_after_from_exception(exc: Exception) -> Optional[float]:
+def _extract_retry_after_from_exception(exc: Exception) -> float | None:
     """
     Extract the Retry-After header from a rate-limit exception for intelligent backoff.
 
@@ -61,7 +60,7 @@ def _extract_retry_after_from_exception(exc: Exception) -> Optional[float]:
     return None
 
 
-def _is_content_filter_error(data: Union[dict[str, object], str]) -> bool:
+def _is_content_filter_error(data: dict[str, object] | str) -> bool:
     """
     Check if error data indicates content filtering.
 
@@ -91,7 +90,7 @@ def _is_content_filter_error(data: Union[dict[str, object], str]) -> bool:
     return "content_filter" in lower or "policy_violation" in lower or "moderation_blocked" in lower
 
 
-def _extract_error_payload(exc: Exception) -> tuple[Union[dict[str, object], str], bool]:
+def _extract_error_payload(exc: Exception) -> tuple[dict[str, object] | str, bool]:
     """
     Extract error payload and detect content filter from an OpenAI SDK exception.
 
diff --git a/pyrit/prompt_target/openai/openai_image_target.py b/pyrit/prompt_target/openai/openai_image_target.py
index 7ae0383998..fec66aabb4 100644
--- a/pyrit/prompt_target/openai/openai_image_target.py
+++ b/pyrit/prompt_target/openai/openai_image_target.py
@@ -2,7 +2,7 @@
 # Licensed under the MIT license.
 import base64
 import logging
-from typing import Any, Literal, Optional
+from typing import Any, Literal
 
 import httpx
 
@@ -65,11 +65,11 @@ def __init__(
             "1792x1024",
             "1024x1792",
         ] = "1024x1024",
-        output_format: Optional[Literal["png", "jpeg", "webp"]] = None,
-        quality: Optional[Literal["auto", "low", "medium", "high", "standard", "hd"]] = None,
-        style: Optional[Literal["natural", "vivid"]] = None,
-        background: Optional[Literal["transparent", "opaque", "auto"]] = None,
-        custom_configuration: Optional[TargetConfiguration] = None,
+        output_format: Literal["png", "jpeg", "webp"] | None = None,
+        quality: Literal["auto", "low", "medium", "high", "standard", "hd"] | None = None,
+        style: Literal["natural", "vivid"] | None = None,
+        background: Literal["transparent", "opaque", "auto"] | None = None,
+        custom_configuration: TargetConfiguration | None = None,
         *args: Any,
         **kwargs: Any,
     ) -> None:
diff --git a/pyrit/prompt_target/openai/openai_realtime_target.py b/pyrit/prompt_target/openai/openai_realtime_target.py
index 0197d5ba64..0c75faa908 100644
--- a/pyrit/prompt_target/openai/openai_realtime_target.py
+++ b/pyrit/prompt_target/openai/openai_realtime_target.py
@@ -6,7 +6,7 @@
 import logging
 import re
 import wave
-from typing import TYPE_CHECKING, Any, ClassVar, Literal, Optional
+from typing import TYPE_CHECKING, Any, ClassVar, Literal
 
 from openai import AsyncOpenAI
 
@@ -87,9 +87,9 @@ class RealtimeTarget(OpenAITarget):
     def __init__(
         self,
         *,
-        voice: Optional[RealTimeVoice] = None,
-        existing_convo: Optional[dict[str, Any]] = None,
-        custom_configuration: Optional[TargetConfiguration] = None,
+        voice: RealTimeVoice | None = None,
+        existing_convo: dict[str, Any] | None = None,
+        custom_configuration: TargetConfiguration | None = None,
         **kwargs: Any,
     ) -> None:
         """
@@ -121,7 +121,7 @@ def __init__(
 
         self.voice = voice
         self._existing_conversation = existing_convo if existing_convo is not None else {}
-        self._realtime_client: Optional[AsyncOpenAI] = None
+        self._realtime_client: AsyncOpenAI | None = None
 
     def open_streaming_session(
         self,
@@ -550,7 +550,7 @@ async def save_audio_async(
         num_channels: int = 1,
         sample_width: int = 2,
         sample_rate: int = 16000,
-        output_filename: Optional[str] = None,
+        output_filename: str | None = None,
     ) -> str:
         """
         Save audio bytes to a WAV file.
@@ -583,7 +583,7 @@ async def save_audio(  # pyrit-async-suffix-exempt
         num_channels: int = 1,
         sample_width: int = 2,
         sample_rate: int = 16000,
-        output_filename: Optional[str] = None,
+        output_filename: str | None = None,
     ) -> str:
         """
         Use ``save_audio_async`` instead; this is a deprecated alias.
diff --git a/pyrit/prompt_target/openai/openai_response_target.py b/pyrit/prompt_target/openai/openai_response_target.py
index c96b0c115a..64428bb6a0 100644
--- a/pyrit/prompt_target/openai/openai_response_target.py
+++ b/pyrit/prompt_target/openai/openai_response_target.py
@@ -8,7 +8,6 @@
 from typing import (
     Any,
     Literal,
-    Optional,
     cast,
 )
 
@@ -91,15 +90,15 @@ class OpenAIResponseTarget(OpenAITarget):
     def __init__(
         self,
         *,
-        custom_functions: Optional[dict[str, ToolExecutor]] = None,
-        max_output_tokens: Optional[int] = None,
-        temperature: Optional[float] = None,
-        top_p: Optional[float] = None,
-        reasoning_effort: Optional[ReasoningEffort] = None,
-        reasoning_summary: Optional[Literal["auto", "concise", "detailed"]] = None,
-        extra_body_parameters: Optional[dict[str, Any]] = None,
+        custom_functions: dict[str, ToolExecutor] | None = None,
+        max_output_tokens: int | None = None,
+        temperature: float | None = None,
+        top_p: float | None = None,
+        reasoning_effort: ReasoningEffort | None = None,
+        reasoning_summary: Literal["auto", "concise", "detailed"] | None = None,
+        extra_body_parameters: dict[str, Any] | None = None,
         fail_on_missing_function: bool = False,
-        custom_configuration: Optional[TargetConfiguration] = None,
+        custom_configuration: TargetConfiguration | None = None,
         **kwargs: Any,
     ) -> None:
         """
@@ -396,7 +395,7 @@ async def _construct_request_body_async(
         # Filter out None values
         return {k: v for k, v in body_parameters.items() if v is not None}
 
-    def _build_reasoning_config(self) -> Optional[dict[str, Any]]:
+    def _build_reasoning_config(self) -> dict[str, Any] | None:
         """
         Build the reasoning configuration dict for the Responses API.
 
@@ -413,7 +412,7 @@ def _build_reasoning_config(self) -> Optional[dict[str, Any]]:
             reasoning["summary"] = self._reasoning_summary
         return reasoning
 
-    def _build_text_format(self, json_config: _JsonResponseConfig) -> Optional[dict[str, Any]]:
+    def _build_text_format(self, json_config: _JsonResponseConfig) -> dict[str, Any] | None:
         if not json_config.enabled:
             return None
 
@@ -459,7 +458,7 @@ def _check_content_filter(self, response: Any) -> bool:
 
         return False
 
-    def _extract_partial_content(self, response: Any) -> Optional[str]:
+    def _extract_partial_content(self, response: Any) -> str | None:
         """
         Extract partial content from a Response API response that was content-filtered.
 
@@ -493,7 +492,7 @@ def _extract_partial_content(self, response: Any) -> Optional[str]:
         except (AttributeError, IndexError, TypeError):
             return None
 
-    def _validate_response(self, response: Any, request: MessagePiece) -> Optional[Message]:
+    def _validate_response(self, response: Any, request: MessagePiece) -> Message | None:
         """
         Validate a Response API response for errors.
 
@@ -584,7 +583,7 @@ async def _send_prompt_to_target_async(self, *, normalized_conversation: list[Me
         responses_to_return: list[Message] = []
 
         # Main agentic loop - each back-and-forth creates a new message
-        tool_call_section: Optional[dict[str, Any]] = None
+        tool_call_section: dict[str, Any] | None = None
 
         while True:
             logger.info(f"Sending conversation with {len(working_conversation)} messages to the prompt target")
@@ -625,7 +624,7 @@ async def _send_prompt_to_target_async(self, *, normalized_conversation: list[Me
         return responses_to_return
 
     def _parse_response_output_section(
-        self, *, section: Any, message_piece: MessagePiece, error: Optional[PromptResponseError]
+        self, *, section: Any, message_piece: MessagePiece, error: PromptResponseError | None
     ) -> MessagePiece | None:
         """
         Parse model output sections, forwarding tool-calls for the agentic loop.
@@ -726,7 +725,7 @@ def _parse_response_output_section(
 
     # Agentic helpers (module scope)
 
-    def _find_last_pending_tool_call(self, reply: Message) -> Optional[dict[str, Any]]:
+    def _find_last_pending_tool_call(self, reply: Message) -> dict[str, Any] | None:
         """
         Return the last tool-call section in assistant messages, or None.
         Looks for a piece whose value parses as JSON with a 'type' key matching function_call.
diff --git a/pyrit/prompt_target/openai/openai_target.py b/pyrit/prompt_target/openai/openai_target.py
index 3ae988f186..acc54103f2 100644
--- a/pyrit/prompt_target/openai/openai_target.py
+++ b/pyrit/prompt_target/openai/openai_target.py
@@ -6,7 +6,7 @@
 import re
 from abc import abstractmethod
 from collections.abc import Awaitable, Callable
-from typing import Any, Optional
+from typing import Any
 from urllib.parse import urlparse
 
 from openai import (
@@ -61,7 +61,7 @@ class OpenAITarget(PromptTarget):
     endpoint_environment_variable: str
     api_key_environment_variable: str
 
-    _async_client: Optional[AsyncOpenAI] = None
+    _async_client: AsyncOpenAI | None = None
 
     @property
     def _client(self) -> AsyncOpenAI:
@@ -78,14 +78,14 @@ def _client(self) -> AsyncOpenAI:
     def __init__(
         self,
         *,
-        model_name: Optional[str] = None,
-        endpoint: Optional[str] = None,
-        api_key: Optional[str | Callable[[], str | Awaitable[str]]] = None,
-        headers: Optional[str] = None,
-        max_requests_per_minute: Optional[int] = None,
-        httpx_client_kwargs: Optional[dict[str, Any]] = None,
-        underlying_model: Optional[str] = None,
-        custom_configuration: Optional[TargetConfiguration] = None,
+        model_name: str | None = None,
+        endpoint: str | None = None,
+        api_key: str | Callable[[], str | Awaitable[str]] | None = None,
+        headers: str | None = None,
+        max_requests_per_minute: int | None = None,
+        httpx_client_kwargs: dict[str, Any] | None = None,
+        underlying_model: str | None = None,
+        custom_configuration: TargetConfiguration | None = None,
     ) -> None:
         """
         Initialize an instance of OpenAITarget.
@@ -583,7 +583,7 @@ def _handle_content_filter_response(self, response: Any, request: MessagePiece)
 
         return error_message
 
-    def _extract_partial_content(self, response: Any) -> Optional[str]:
+    def _extract_partial_content(self, response: Any) -> str | None:
         """
         Extract any partial content the model generated before the content filter triggered.
 
@@ -598,7 +598,7 @@ def _extract_partial_content(self, response: Any) -> Optional[str]:
         """
         return None
 
-    def _validate_response(self, response: Any, request: MessagePiece) -> Optional[Message]:
+    def _validate_response(self, response: Any, request: MessagePiece) -> Message | None:
         """
         Validate the response and return error Message if needed.
 
diff --git a/pyrit/prompt_target/openai/openai_tts_target.py b/pyrit/prompt_target/openai/openai_tts_target.py
index d9c66128cb..eaa6101c75 100644
--- a/pyrit/prompt_target/openai/openai_tts_target.py
+++ b/pyrit/prompt_target/openai/openai_tts_target.py
@@ -2,7 +2,7 @@
 # Licensed under the MIT license.
 
 import logging
-from typing import Any, Literal, Optional
+from typing import Any, Literal
 
 from pyrit.exceptions import (
     pyrit_target_retry,
@@ -40,8 +40,8 @@ def __init__(
         voice: TTSVoice = "alloy",
         response_format: TTSResponseFormat = "mp3",
         language: str = "en",
-        speed: Optional[float] = None,
-        custom_configuration: Optional[TargetConfiguration] = None,
+        speed: float | None = None,
+        custom_configuration: TargetConfiguration | None = None,
         **kwargs: Any,
     ) -> None:
         """
diff --git a/pyrit/prompt_target/openai/openai_video_target.py b/pyrit/prompt_target/openai/openai_video_target.py
index 37dedc9ae0..db8deadf35 100644
--- a/pyrit/prompt_target/openai/openai_video_target.py
+++ b/pyrit/prompt_target/openai/openai_video_target.py
@@ -4,7 +4,7 @@
 import logging
 from mimetypes import guess_type
 from pathlib import Path
-from typing import Any, Optional, Union, cast
+from typing import Any, cast
 
 from openai.types import VideoSeconds, VideoSize
 
@@ -67,7 +67,7 @@ def __init__(
         *,
         resolution_dimensions: VideoSize = "1280x720",
         n_seconds: int | VideoSeconds = 4,
-        custom_configuration: Optional[TargetConfiguration] = None,
+        custom_configuration: TargetConfiguration | None = None,
         **kwargs: Any,
     ) -> None:
         """
@@ -428,7 +428,7 @@ async def _construct_message_from_response_async(self, response: Any, request: A
         )
 
     async def _save_video_response_async(
-        self, *, request: MessagePiece, video_data: bytes, video_id: Optional[str] = None
+        self, *, request: MessagePiece, video_data: bytes, video_id: str | None = None
     ) -> Message:
         """
         Save video data to storage and construct response.
@@ -449,7 +449,7 @@ async def _save_video_response_async(
         logger.info(f"Video saved to: {video_path}")
 
         # Include video_id in metadata for chaining (e.g., remix the generated video later)
-        prompt_metadata: Optional[dict[str, Union[str, int]]] = {"video_id": video_id} if video_id else None
+        prompt_metadata: dict[str, str | int] | None = {"video_id": video_id} if video_id else None
 
         # Construct response
         return construct_response_from_request(
diff --git a/pyrit/prompt_target/playwright_copilot_target.py b/pyrit/prompt_target/playwright_copilot_target.py
index a2dfc796b2..0a7021c23c 100644
--- a/pyrit/prompt_target/playwright_copilot_target.py
+++ b/pyrit/prompt_target/playwright_copilot_target.py
@@ -7,7 +7,7 @@
 from contextlib import suppress
 from dataclasses import dataclass
 from enum import Enum
-from typing import TYPE_CHECKING, Any, Optional, Union
+from typing import TYPE_CHECKING, Any
 
 from pyrit.models import (
     ComponentIdentifier,
@@ -128,7 +128,7 @@ def __init__(
         *,
         page: "Page",
         copilot_type: CopilotType = CopilotType.CONSUMER,
-        custom_configuration: Optional[TargetConfiguration] = None,
+        custom_configuration: TargetConfiguration | None = None,
     ) -> None:
         """
         Initialize the Playwright Copilot target.
@@ -254,7 +254,7 @@ async def _send_prompt_to_target_async(self, *, normalized_conversation: list[Me
 
         return [response_entry]
 
-    async def _interact_with_copilot_async(self, message: Message) -> Union[str, list[tuple[str, PromptDataType]]]:
+    async def _interact_with_copilot_async(self, message: Message) -> str | list[tuple[str, PromptDataType]]:
         """
         Interact with Microsoft Copilot interface to send multimodal prompts.
 
@@ -276,9 +276,7 @@ async def _interact_with_copilot_async(self, message: Message) -> Union[str, lis
 
         return await self._wait_for_response_async(selectors)
 
-    async def _wait_for_response_async(
-        self, selectors: CopilotSelectors
-    ) -> Union[str, list[tuple[str, PromptDataType]]]:
+    async def _wait_for_response_async(self, selectors: CopilotSelectors) -> str | list[tuple[str, PromptDataType]]:
         """
         Wait for Copilot's response and extract the text and/or images.
 
@@ -332,7 +330,7 @@ async def _wait_for_response_async(
 
     async def _extract_content_if_ready_async(
         self, selectors: CopilotSelectors, initial_group_count: int
-    ) -> Union[str, list[tuple[str, PromptDataType]], None]:
+    ) -> str | list[tuple[str, PromptDataType]] | None:
         """
         Extract content if ready, otherwise return None.
 
@@ -733,7 +731,7 @@ async def _extract_fallback_text_async(self, *, ai_message_groups: list[Any]) ->
 
     def _assemble_response(
         self, *, response_pieces: list[tuple[str, PromptDataType]]
-    ) -> Union[str, list[tuple[str, PromptDataType]]]:
+    ) -> str | list[tuple[str, PromptDataType]]:
         """
         Assemble response pieces into appropriate return format.
 
@@ -755,7 +753,7 @@ def _assemble_response(
 
     async def _extract_multimodal_content_async(
         self, selectors: CopilotSelectors, initial_group_count: int = 0
-    ) -> Union[str, list[tuple[str, PromptDataType]]]:
+    ) -> str | list[tuple[str, PromptDataType]]:
         """
         Extract multimodal content (text and images) from Copilot response.
 
diff --git a/pyrit/prompt_target/playwright_target.py b/pyrit/prompt_target/playwright_target.py
index 4178fe902b..d33ba2736c 100644
--- a/pyrit/prompt_target/playwright_target.py
+++ b/pyrit/prompt_target/playwright_target.py
@@ -1,7 +1,7 @@
 # Copyright (c) Microsoft Corporation.
 # Licensed under the MIT license.
 
-from typing import TYPE_CHECKING, Optional, Protocol
+from typing import TYPE_CHECKING, Protocol
 
 from pyrit.models import (
     Message,
@@ -71,8 +71,8 @@ def __init__(
         *,
         interaction_func: InteractionFunction,
         page: "Page",
-        max_requests_per_minute: Optional[int] = None,
-        custom_configuration: Optional[TargetConfiguration] = None,
+        max_requests_per_minute: int | None = None,
+        custom_configuration: TargetConfiguration | None = None,
     ) -> None:
         """
         Initialize the Playwright target.
diff --git a/pyrit/prompt_target/prompt_shield_target.py b/pyrit/prompt_target/prompt_shield_target.py
index 74c465a91a..d64af0de57 100644
--- a/pyrit/prompt_target/prompt_shield_target.py
+++ b/pyrit/prompt_target/prompt_shield_target.py
@@ -4,7 +4,7 @@
 import json
 import logging
 from collections.abc import Callable
-from typing import Any, Literal, Optional
+from typing import Any, Literal
 
 from pyrit.common import default_values, net_utility
 from pyrit.models import (
@@ -56,12 +56,12 @@ class PromptShieldTarget(PromptTarget):
 
     def __init__(
         self,
-        endpoint: Optional[str] = None,
-        api_key: Optional[str | Callable[[], str]] = None,
-        api_version: Optional[str] = "2024-09-01",
-        field: Optional[PromptShieldEntryField] = None,
-        max_requests_per_minute: Optional[int] = None,
-        custom_configuration: Optional[TargetConfiguration] = None,
+        endpoint: str | None = None,
+        api_key: str | Callable[[], str] | None = None,
+        api_version: str | None = "2024-09-01",
+        field: PromptShieldEntryField | None = None,
+        max_requests_per_minute: int | None = None,
+        custom_configuration: TargetConfiguration | None = None,
     ) -> None:
         """
         Class that initializes an Azure Content Safety Prompt Shield Target.
diff --git a/pyrit/prompt_target/text_target.py b/pyrit/prompt_target/text_target.py
index 9ede8d9ddc..8e0deed295 100644
--- a/pyrit/prompt_target/text_target.py
+++ b/pyrit/prompt_target/text_target.py
@@ -5,7 +5,7 @@
 import json
 import sys
 from pathlib import Path
-from typing import IO, Optional
+from typing import IO
 
 from pyrit.common.deprecation import print_deprecation_message
 from pyrit.models import Message, MessagePiece
@@ -26,7 +26,7 @@ def __init__(
         self,
         *,
         text_stream: IO[str] = sys.stdout,
-        custom_configuration: Optional[TargetConfiguration] = None,
+        custom_configuration: TargetConfiguration | None = None,
     ) -> None:
         """
         Initialize the TextTarget.
diff --git a/pyrit/prompt_target/websocket_copilot_target.py b/pyrit/prompt_target/websocket_copilot_target.py
index 6a5de15f60..0635971011 100644
--- a/pyrit/prompt_target/websocket_copilot_target.py
+++ b/pyrit/prompt_target/websocket_copilot_target.py
@@ -7,7 +7,7 @@
 import pathlib
 import uuid
 from enum import IntEnum
-from typing import Any, Optional, Union
+from typing import Any
 
 import httpx
 import websockets
@@ -90,11 +90,11 @@ def __init__(
         self,
         *,
         websocket_base_url: str = "wss://substrate.office.com/m365Copilot/Chathub",
-        max_requests_per_minute: Optional[int] = None,
+        max_requests_per_minute: int | None = None,
         model_name: str = "copilot",
         response_timeout_seconds: int = RESPONSE_TIMEOUT_SECONDS,
-        authenticator: Optional[Union[CopilotAuthenticator, ManualCopilotAuthenticator]] = None,
-        custom_configuration: Optional[TargetConfiguration] = None,
+        authenticator: CopilotAuthenticator | ManualCopilotAuthenticator | None = None,
+        custom_configuration: TargetConfiguration | None = None,
     ) -> None:
         """
         Initialize the WebSocketCopilotTarget.
diff --git a/pyrit/registry/base.py b/pyrit/registry/base.py
index cdff9067f1..11e98d8787 100644
--- a/pyrit/registry/base.py
+++ b/pyrit/registry/base.py
@@ -11,7 +11,7 @@
 from __future__ import annotations
 
 from dataclasses import dataclass
-from typing import TYPE_CHECKING, Any, Optional, Protocol, TypeVar, runtime_checkable
+from typing import TYPE_CHECKING, Any, Protocol, TypeVar, runtime_checkable
 
 if TYPE_CHECKING:
     from collections.abc import Iterator
@@ -88,8 +88,8 @@ def get_names(self) -> list[str]:
     def list_metadata(
         self,
         *,
-        include_filters: Optional[dict[str, Any]] = None,
-        exclude_filters: Optional[dict[str, Any]] = None,
+        include_filters: dict[str, Any] | None = None,
+        exclude_filters: dict[str, Any] | None = None,
     ) -> list[MetadataT]:
         """
         List metadata for all registered items, optionally filtered.
@@ -148,8 +148,8 @@ def _get_metadata_value(metadata: Any, key: str) -> tuple[bool, Any]:
 def _matches_filters(
     metadata: Any,
     *,
-    include_filters: Optional[dict[str, Any]] = None,
-    exclude_filters: Optional[dict[str, Any]] = None,
+    include_filters: dict[str, Any] | None = None,
+    exclude_filters: dict[str, Any] | None = None,
 ) -> bool:
     """
     Check if a metadata object matches all provided filters.
diff --git a/pyrit/registry/class_registries/base_class_registry.py b/pyrit/registry/class_registries/base_class_registry.py
index 85211aba84..4a2f504d7a 100644
--- a/pyrit/registry/class_registries/base_class_registry.py
+++ b/pyrit/registry/class_registries/base_class_registry.py
@@ -19,7 +19,7 @@
 from __future__ import annotations
 
 from abc import ABC, abstractmethod
-from typing import TYPE_CHECKING, Generic, Optional, TypeVar
+from typing import TYPE_CHECKING, Generic, TypeVar
 
 if TYPE_CHECKING:
     from collections.abc import Callable, Iterator
@@ -54,8 +54,8 @@ def __init__(
         self,
         *,
         registered_class: type[T],
-        factory: Optional[Callable[..., T]] = None,
-        default_kwargs: Optional[dict[str, object]] = None,
+        factory: Callable[..., T] | None = None,
+        default_kwargs: dict[str, object] | None = None,
     ) -> None:
         """
         Initialize a class entry.
@@ -129,7 +129,7 @@ def __init__(self, *, lazy_discovery: bool = True) -> None:
         """
         # Maps registry names to ClassEntry wrappers
         self._class_entries: dict[str, ClassEntry[T]] = {}
-        self._metadata_cache: Optional[list[MetadataT]] = None
+        self._metadata_cache: list[MetadataT] | None = None
         self._discovered = False
         self._lazy_discovery = lazy_discovery
 
@@ -211,7 +211,7 @@ def get_class(self, name: str) -> type[T]:
             raise KeyError(f"'{name}' not found in registry. Available: {available}")
         return entry.registered_class
 
-    def get_entry(self, name: str) -> Optional[ClassEntry[T]]:
+    def get_entry(self, name: str) -> ClassEntry[T] | None:
         """
         Get the full ClassEntry for a registered class.
 
@@ -242,8 +242,8 @@ def get_names(self) -> list[str]:
     def list_metadata(
         self,
         *,
-        include_filters: Optional[dict[str, object]] = None,
-        exclude_filters: Optional[dict[str, object]] = None,
+        include_filters: dict[str, object] | None = None,
+        exclude_filters: dict[str, object] | None = None,
     ) -> list[MetadataT]:
         """
         List metadata for all registered classes, optionally filtered.
@@ -286,9 +286,9 @@ def register(
         self,
         cls: type[T],
         *,
-        name: Optional[str] = None,
-        factory: Optional[Callable[..., T]] = None,
-        default_kwargs: Optional[dict[str, object]] = None,
+        name: str | None = None,
+        factory: Callable[..., T] | None = None,
+        default_kwargs: dict[str, object] | None = None,
     ) -> None:
         """
         Register a class with the registry.
diff --git a/pyrit/registry/class_registries/initializer_registry.py b/pyrit/registry/class_registries/initializer_registry.py
index 17fb39fb7c..5310af3d69 100644
--- a/pyrit/registry/class_registries/initializer_registry.py
+++ b/pyrit/registry/class_registries/initializer_registry.py
@@ -15,7 +15,7 @@
 import logging
 from dataclasses import dataclass, field
 from pathlib import Path
-from typing import TYPE_CHECKING, Optional
+from typing import TYPE_CHECKING
 
 from pyrit.models import class_name_to_snake_case, validate_registry_name
 from pyrit.registry.base import ClassRegistryEntry
@@ -47,7 +47,7 @@ class InitializerMetadata(ClassRegistryEntry):
     required_env_vars: tuple[str, ...] = field(kw_only=True)
 
     # Supported parameters as tuples of (name, description, default).
-    supported_parameters: tuple[tuple[str, str, Optional[list[str]]], ...] = field(kw_only=True, default=())
+    supported_parameters: tuple[tuple[str, str, list[str] | None], ...] = field(kw_only=True, default=())
 
 
 class InitializerRegistry(BaseClassRegistry["PyRITInitializer", InitializerMetadata]):
@@ -61,7 +61,7 @@ class InitializerRegistry(BaseClassRegistry["PyRITInitializer", InitializerMetad
     The directory structure is used for organization but not exposed to users.
     """
 
-    def __init__(self, *, discovery_path: Optional[Path] = None, lazy_discovery: bool = False) -> None:
+    def __init__(self, *, discovery_path: Path | None = None, lazy_discovery: bool = False) -> None:
         """
         Initialize the initializer registry.
 
diff --git a/pyrit/registry/class_registries/scenario_registry.py b/pyrit/registry/class_registries/scenario_registry.py
index 2702b1860e..0300b00a06 100644
--- a/pyrit/registry/class_registries/scenario_registry.py
+++ b/pyrit/registry/class_registries/scenario_registry.py
@@ -13,7 +13,7 @@
 import logging
 from dataclasses import dataclass, field
 from pathlib import Path
-from typing import TYPE_CHECKING, Any, NamedTuple, Optional, get_origin
+from typing import TYPE_CHECKING, Any, NamedTuple, get_origin
 
 from pyrit.models import class_name_to_snake_case
 from pyrit.registry.base import ClassRegistryEntry
@@ -53,7 +53,7 @@ class ScenarioMetadata(ClassRegistryEntry):
     default_datasets: tuple[str, ...] = field(kw_only=True)
 
     # Maximum number of items per dataset.
-    max_dataset_size: Optional[int] = field(kw_only=True)
+    max_dataset_size: int | None = field(kw_only=True)
 
     # Scenario-declared custom parameters.
     supported_parameters: tuple[ScenarioParameterMetadata, ...] = field(kw_only=True, default=())
@@ -71,7 +71,7 @@ class ScenarioParameterMetadata(NamedTuple):
     description: str
     default: Any
     param_type: str
-    choices: Optional[list[str]]
+    choices: list[str] | None
     is_list: bool = False
 
 
diff --git a/pyrit/registry/discovery.py b/pyrit/registry/discovery.py
index 5df0c14fee..34c1562bc3 100644
--- a/pyrit/registry/discovery.py
+++ b/pyrit/registry/discovery.py
@@ -15,7 +15,7 @@
 import pkgutil
 from collections.abc import Callable, Iterator
 from pathlib import Path
-from typing import Optional, TypeVar
+from typing import TypeVar
 
 logger = logging.getLogger(__name__)
 
@@ -92,7 +92,7 @@ def discover_in_package(
     package_name: str,
     base_class: type[T],
     recursive: bool = True,
-    name_builder: Optional[Callable[[str, str], str]] = None,
+    name_builder: Callable[[str, str], str] | None = None,
     _prefix: str = "",
 ) -> Iterator[tuple[str, type[T]]]:
     """
@@ -156,7 +156,7 @@ def name_builder(prefix: str, name: str) -> str:
 def discover_subclasses_in_loaded_modules(
     *,
     base_class: type[T],
-    exclude_module_prefixes: Optional[tuple[str, ...]] = None,
+    exclude_module_prefixes: tuple[str, ...] | None = None,
 ) -> Iterator[tuple[str, type[T]]]:
     """
     Discover subclasses of a base class from already-loaded modules.
diff --git a/pyrit/registry/object_registries/converter_registry.py b/pyrit/registry/object_registries/converter_registry.py
index 4d83c9e1fd..568d1e6332 100644
--- a/pyrit/registry/object_registries/converter_registry.py
+++ b/pyrit/registry/object_registries/converter_registry.py
@@ -12,7 +12,7 @@
 from __future__ import annotations
 
 import logging
-from typing import TYPE_CHECKING, Optional, Union
+from typing import TYPE_CHECKING
 
 from pyrit.registry.object_registries.retrievable_instance_registry import (
     RetrievableInstanceRegistry,
@@ -37,8 +37,8 @@ def register_instance(
         self,
         converter: PromptConverter,
         *,
-        name: Optional[str] = None,
-        tags: Optional[Union[dict[str, str], list[str]]] = None,
+        name: str | None = None,
+        tags: dict[str, str] | list[str] | None = None,
     ) -> None:
         """
         Register a converter instance.
@@ -56,7 +56,7 @@ def register_instance(
         self.register(converter, name=name, tags=tags)
         logger.debug(f"Registered converter instance: {name} ({converter.__class__.__name__})")
 
-    def get_instance_by_name(self, name: str) -> Optional[PromptConverter]:
+    def get_instance_by_name(self, name: str) -> PromptConverter | None:
         """
         Get a registered converter instance by name.
 
diff --git a/pyrit/registry/object_registries/scorer_registry.py b/pyrit/registry/object_registries/scorer_registry.py
index af5c59946f..d1a938aa30 100644
--- a/pyrit/registry/object_registries/scorer_registry.py
+++ b/pyrit/registry/object_registries/scorer_registry.py
@@ -10,7 +10,7 @@
 from __future__ import annotations
 
 import logging
-from typing import TYPE_CHECKING, Optional, Union
+from typing import TYPE_CHECKING
 
 from pyrit.registry.object_registries.retrievable_instance_registry import (
     RetrievableInstanceRegistry,
@@ -38,8 +38,8 @@ def register_instance(
         self,
         scorer: Scorer,
         *,
-        name: Optional[str] = None,
-        tags: Optional[Union[dict[str, str], list[str]]] = None,
+        name: str | None = None,
+        tags: dict[str, str] | list[str] | None = None,
     ) -> None:
         """
         Register a scorer instance.
@@ -60,7 +60,7 @@ def register_instance(
         self.register(scorer, name=name, tags=tags)
         logger.debug(f"Registered scorer instance: {name} ({scorer.__class__.__name__})")
 
-    def get_instance_by_name(self, name: str) -> Optional[Scorer]:
+    def get_instance_by_name(self, name: str) -> Scorer | None:
         """
         Get a registered scorer instance by name.
 
diff --git a/pyrit/registry/object_registries/target_registry.py b/pyrit/registry/object_registries/target_registry.py
index c6fefd3926..170bad2078 100644
--- a/pyrit/registry/object_registries/target_registry.py
+++ b/pyrit/registry/object_registries/target_registry.py
@@ -10,7 +10,7 @@
 from __future__ import annotations
 
 import logging
-from typing import TYPE_CHECKING, Optional, Union
+from typing import TYPE_CHECKING
 
 from pyrit.registry.object_registries.retrievable_instance_registry import (
     RetrievableInstanceRegistry,
@@ -38,8 +38,8 @@ def register_instance(
         self,
         target: PromptTarget,
         *,
-        name: Optional[str] = None,
-        tags: Optional[Union[dict[str, str], list[str]]] = None,
+        name: str | None = None,
+        tags: dict[str, str] | list[str] | None = None,
     ) -> None:
         """
         Register a target instance.
@@ -61,7 +61,7 @@ def register_instance(
         self.register(target, name=name, tags=tags)
         logger.debug(f"Registered target instance: {name} ({target.__class__.__name__})")
 
-    def get_instance_by_name(self, name: str) -> Optional[PromptTarget]:
+    def get_instance_by_name(self, name: str) -> PromptTarget | None:
         """
         Get a registered target instance by name.
 
diff --git a/pyrit/scenario/core/atomic_attack.py b/pyrit/scenario/core/atomic_attack.py
index acec06f8b0..d247058c8f 100644
--- a/pyrit/scenario/core/atomic_attack.py
+++ b/pyrit/scenario/core/atomic_attack.py
@@ -59,7 +59,7 @@ def __init__(
         seed_groups: list[SeedAttackGroup],
         adversarial_chat: Optional["PromptTarget"] = None,
         objective_scorer: Optional["TrueFalseScorer"] = None,
-        memory_labels: Optional[dict[str, str]] = None,
+        memory_labels: dict[str, str] | None = None,
         **attack_execute_params: Any,
     ) -> None:
         """
diff --git a/pyrit/scenario/core/dataset_configuration.py b/pyrit/scenario/core/dataset_configuration.py
index 25cd9162c3..cbc22df444 100644
--- a/pyrit/scenario/core/dataset_configuration.py
+++ b/pyrit/scenario/core/dataset_configuration.py
@@ -11,7 +11,7 @@
 from __future__ import annotations
 
 import random
-from typing import TYPE_CHECKING, Optional
+from typing import TYPE_CHECKING
 
 from pyrit.memory import CentralMemory
 from pyrit.models import SeedAttackGroup, SeedGroup
@@ -46,10 +46,10 @@ class DatasetConfiguration:
     def __init__(
         self,
         *,
-        seed_groups: Optional[list[SeedGroup]] = None,
-        dataset_names: Optional[list[str]] = None,
-        max_dataset_size: Optional[int] = None,
-        scenario_strategies: Optional[Sequence[ScenarioStrategy]] = None,
+        seed_groups: list[SeedGroup] | None = None,
+        dataset_names: list[str] | None = None,
+        max_dataset_size: int | None = None,
+        scenario_strategies: Sequence[ScenarioStrategy] | None = None,
     ) -> None:
         """
         Initialize a DatasetConfiguration.
diff --git a/pyrit/scenario/core/scenario.py b/pyrit/scenario/core/scenario.py
index 2238886cdb..67dcd01cb7 100644
--- a/pyrit/scenario/core/scenario.py
+++ b/pyrit/scenario/core/scenario.py
@@ -18,7 +18,7 @@
 from collections.abc import Sequence
 from enum import Enum
 from pathlib import Path
-from typing import TYPE_CHECKING, Any, ClassVar, Optional, Union, cast, get_origin
+from typing import TYPE_CHECKING, Any, ClassVar, cast, get_origin
 
 try:
     # Built-in on Python 3.11+. Fall back to the ``exceptiongroup`` backport on 3.10
@@ -177,7 +177,7 @@ def __init__(
         default_strategy: ScenarioStrategy,
         default_dataset_config: DatasetConfiguration,
         objective_scorer: Scorer,
-        scenario_result_id: Optional[Union[uuid.UUID, str]] = None,
+        scenario_result_id: uuid.UUID | str | None = None,
         include_default_baseline: bool | None = None,  # Deprecated. Will be removed in 0.16.0.
     ) -> None:
         """
@@ -223,10 +223,10 @@ def __init__(
         self._default_dataset_config = default_dataset_config
 
         # These will be set in initialize_async
-        self._objective_target: Optional[PromptTarget] = None
-        self._objective_target_identifier: Optional[ComponentIdentifier] = None
+        self._objective_target: PromptTarget | None = None
+        self._objective_target_identifier: ComponentIdentifier | None = None
         self._memory_labels: dict[str, str] = {}
-        self._max_concurrency: Optional[int] = None
+        self._max_concurrency: int | None = None
         self._max_retries: int = 0
 
         self._objective_scorer = objective_scorer
@@ -235,7 +235,7 @@ def __init__(
         self._name = name if name else type(self).__name__
         self._memory = CentralMemory.get_memory_instance()
         self._atomic_attacks: list[AtomicAttack] = []
-        self._scenario_result_id: Optional[str] = str(scenario_result_id) if scenario_result_id else None
+        self._scenario_result_id: str | None = str(scenario_result_id) if scenario_result_id else None
 
         # Store prepared strategies for use in _get_atomic_attacks_async
         self._scenario_strategies: list[ScenarioStrategy] = []
@@ -533,7 +533,7 @@ def _validate_params(self, *, params: dict[str, Any], declared: list[Parameter])
 
     def _prepare_strategies(
         self,
-        strategies: Optional[Sequence[ScenarioStrategy]],
+        strategies: Sequence[ScenarioStrategy] | None,
     ) -> list[ScenarioStrategy]:
         """
         Resolve strategy inputs into a concrete list for this scenario.
@@ -558,11 +558,11 @@ async def initialize_async(
         self,
         *,
         objective_target: PromptTarget = REQUIRED_VALUE,  # type: ignore[ty:invalid-parameter-default]
-        scenario_strategies: Optional[Sequence[ScenarioStrategy]] = None,
-        dataset_config: Optional[DatasetConfiguration] = None,
+        scenario_strategies: Sequence[ScenarioStrategy] | None = None,
+        dataset_config: DatasetConfiguration | None = None,
         max_concurrency: int = 4,
         max_retries: int = 0,
-        memory_labels: Optional[dict[str, str]] = None,
+        memory_labels: dict[str, str] | None = None,
         include_baseline: bool | None = None,
     ) -> None:
         """
@@ -1413,7 +1413,7 @@ def _collect_errors_from_outcomes(
         for outcome in outcomes:
             if isinstance(outcome, BaseException):
                 logger.error(f"Atomic attack failed in scenario '{self._name}': {str(outcome)}")
-                error: Optional[BaseException] = outcome
+                error: BaseException | None = outcome
             else:
                 atomic_attack, atomic_results = outcome
                 error = self._partial_result_to_exception(atomic_attack=atomic_attack, atomic_results=atomic_results)
diff --git a/pyrit/scenario/scenarios/airt/jailbreak.py b/pyrit/scenario/scenarios/airt/jailbreak.py
index 935b81b51f..f7f8f4c351 100644
--- a/pyrit/scenario/scenarios/airt/jailbreak.py
+++ b/pyrit/scenario/scenarios/airt/jailbreak.py
@@ -2,7 +2,7 @@
 # Licensed under the MIT license.
 
 from pathlib import Path
-from typing import Any, Optional, Union
+from typing import Any
 
 from pyrit.common import apply_defaults
 from pyrit.common.deprecation import print_deprecation_message  # Deprecated. Will be removed in 0.16.0.
@@ -90,9 +90,9 @@ def required_datasets(cls) -> list[str]:
     def __init__(
         self,
         *,
-        objective_scorer: Optional[TrueFalseScorer] = None,
-        scenario_result_id: Optional[str] = None,
-        num_templates: Optional[int] = None,
+        objective_scorer: TrueFalseScorer | None = None,
+        scenario_result_id: str | None = None,
+        num_templates: int | None = None,
         num_attempts: int = 1,
         jailbreak_names: list[str] | None = None,
         include_baseline: bool | None = None,  # Deprecated. Will be removed in 0.16.0.
@@ -132,7 +132,7 @@ def __init__(
 
         self._num_templates = num_templates
         self._num_attempts = num_attempts
-        self._adversarial_target: Optional[PromptTarget] = None
+        self._adversarial_target: PromptTarget | None = None
 
         # Note that num_templates and jailbreak_names are mutually exclusive.
         # If self._num_templates is None, then this returns all discoverable jailbreak templates.
@@ -170,7 +170,7 @@ def __init__(
             self._legacy_include_baseline = include_baseline
 
         # Will be resolved in _get_atomic_attacks_async
-        self._seed_groups: Optional[list[SeedAttackGroup]] = None
+        self._seed_groups: list[SeedAttackGroup] | None = None
 
     def _get_or_create_adversarial_target(self) -> PromptTarget:
         """
@@ -233,7 +233,7 @@ async def _get_atomic_attack_from_strategy_async(
             request_converters=PromptConverterConfiguration.from_converters(converters=[jailbreak_converter])
         )
 
-        attack: Optional[Union[ManyShotJailbreakAttack, PromptSendingAttack, RolePlayAttack, SkeletonKeyAttack]] = None
+        attack: ManyShotJailbreakAttack | PromptSendingAttack | RolePlayAttack | SkeletonKeyAttack | None = None
         args: dict[str, Any] = {
             "objective_target": self._objective_target,
             "attack_scoring_config": AttackScoringConfig(objective_scorer=self._objective_scorer),
diff --git a/pyrit/scenario/scenarios/airt/psychosocial.py b/pyrit/scenario/scenarios/airt/psychosocial.py
index 8ba3991649..df39ff23c6 100644
--- a/pyrit/scenario/scenarios/airt/psychosocial.py
+++ b/pyrit/scenario/scenarios/airt/psychosocial.py
@@ -4,7 +4,7 @@
 import logging
 import pathlib
 from dataclasses import dataclass
-from typing import Any, Optional, TypeVar
+from typing import Any, TypeVar
 
 import yaml
 
@@ -73,7 +73,7 @@ class ResolvedSeedData:
     """Helper dataclass for resolved seed data."""
 
     seed_groups: list[SeedAttackGroup]
-    subharm: Optional[str]
+    subharm: str | None
 
 
 class PsychosocialStrategy(ScenarioStrategy):
@@ -97,7 +97,7 @@ class PsychosocialStrategy(ScenarioStrategy):
     LicensedTherapist = ("licensed_therapist", set[str]())
 
     @property
-    def harm_category_filter(self) -> Optional[str]:
+    def harm_category_filter(self) -> str | None:
         """
         Get the harm category filter for this strategy.
 
@@ -179,11 +179,11 @@ class Psychosocial(Scenario):
     def __init__(
         self,
         *,
-        objectives: Optional[list[str]] = None,
-        adversarial_chat: Optional[PromptTarget] = None,
-        objective_scorer: Optional[FloatScaleThresholdScorer] = None,
-        scenario_result_id: Optional[str] = None,
-        subharm_configs: Optional[dict[str, SubharmConfig]] = None,
+        objectives: list[str] | None = None,
+        adversarial_chat: PromptTarget | None = None,
+        objective_scorer: FloatScaleThresholdScorer | None = None,
+        scenario_result_id: str | None = None,
+        subharm_configs: dict[str, SubharmConfig] | None = None,
         max_turns: int = 5,
         include_baseline: bool | None = None,  # Deprecated. Will be removed in 0.16.0.
     ) -> None:
@@ -255,7 +255,7 @@ def __init__(
         # Store deprecated objectives for later resolution in _resolve_seed_groups
         self._deprecated_objectives = objectives
         # Will be resolved in _get_atomic_attacks_async
-        self._seed_groups: Optional[list[SeedAttackGroup]] = None
+        self._seed_groups: list[SeedAttackGroup] | None = None
 
     def _resolve_seed_groups(self) -> ResolvedSeedData:
         """
@@ -300,7 +300,7 @@ def _resolve_seed_groups(self) -> ResolvedSeedData:
             subharm=harm_category_filter,
         )
 
-    def _extract_harm_category_filter(self) -> Optional[str]:
+    def _extract_harm_category_filter(self) -> str | None:
         """
         Extract harm category filter from scenario strategies.
 
@@ -339,7 +339,7 @@ def _filter_by_harm_category(
                 filtered_groups.append(SeedAttackGroup(seeds=filtered_seeds))
         return filtered_groups
 
-    def _get_scorer(self, subharm: Optional[str] = None) -> FloatScaleThresholdScorer:
+    def _get_scorer(self, subharm: str | None = None) -> FloatScaleThresholdScorer:
         """
         Create scorer for psychosocial harms evaluation.
 
@@ -420,7 +420,7 @@ async def _get_atomic_attacks_async(self) -> list[AtomicAttack]:
 
         return atomic_attacks
 
-    def _create_scoring_config(self, subharm: Optional[str]) -> AttackScoringConfig:
+    def _create_scoring_config(self, subharm: str | None) -> AttackScoringConfig:
         subharm_config = self._subharm_configs.get(subharm) if subharm else None
         scorer = self._get_scorer(subharm=subharm) if subharm_config else self._objective_scorer
         return AttackScoringConfig(objective_scorer=scorer)
@@ -470,7 +470,7 @@ def _create_multi_turn_attack(
         self,
         *,
         scoring_config: AttackScoringConfig,
-        subharm: Optional[str],
+        subharm: str | None,
         seed_groups: list[SeedAttackGroup],
     ) -> AtomicAttack:
         subharm_config = self._subharm_configs.get(subharm) if subharm else None
diff --git a/pyrit/scenario/scenarios/airt/scam.py b/pyrit/scenario/scenarios/airt/scam.py
index ab05c0fc81..9e6dca8fbe 100644
--- a/pyrit/scenario/scenarios/airt/scam.py
+++ b/pyrit/scenario/scenarios/airt/scam.py
@@ -3,7 +3,7 @@
 
 import logging
 from pathlib import Path
-from typing import TYPE_CHECKING, Any, Optional
+from typing import TYPE_CHECKING, Any
 
 from pyrit.common import Parameter, apply_defaults
 from pyrit.common.deprecation import print_deprecation_message  # Deprecated. Will be removed in 0.16.0.
@@ -121,9 +121,9 @@ def supported_parameters(cls) -> list[Parameter]:
     def __init__(
         self,
         *,
-        objective_scorer: Optional[TrueFalseScorer] = None,
-        adversarial_chat: Optional[PromptTarget] = None,
-        scenario_result_id: Optional[str] = None,
+        objective_scorer: TrueFalseScorer | None = None,
+        adversarial_chat: PromptTarget | None = None,
+        scenario_result_id: str | None = None,
         include_baseline: bool | None = None,  # Deprecated. Will be removed in 0.16.0.
     ) -> None:
         """
@@ -166,7 +166,7 @@ def __init__(
             self._legacy_include_baseline = include_baseline
 
         # Will be resolved in _get_atomic_attacks_async
-        self._seed_groups: Optional[list[SeedAttackGroup]] = None
+        self._seed_groups: list[SeedAttackGroup] | None = None
 
     def _resolve_seed_groups(self) -> list[SeedAttackGroup]:
         """
@@ -201,7 +201,7 @@ def _get_atomic_attack_from_strategy(self, strategy: str) -> AtomicAttack:
             raise ValueError(
                 "Scenario not properly initialized. Call await scenario.initialize_async() before running."
             )
-        attack_strategy: Optional[AttackStrategy[Any, Any]] = None
+        attack_strategy: AttackStrategy[Any, Any] | None = None
 
         if strategy == "persuasive_rta":
             # Set system prompt to generic persuasion persona
diff --git a/pyrit/scenario/scenarios/foundry/red_team_agent.py b/pyrit/scenario/scenarios/foundry/red_team_agent.py
index 142aa53959..dc14cac8c4 100644
--- a/pyrit/scenario/scenarios/foundry/red_team_agent.py
+++ b/pyrit/scenario/scenarios/foundry/red_team_agent.py
@@ -13,7 +13,7 @@
 from collections.abc import Sequence
 from dataclasses import dataclass, field
 from inspect import signature
-from typing import TYPE_CHECKING, Any, Optional, TypeVar, cast
+from typing import TYPE_CHECKING, Any, TypeVar, cast
 
 from pyrit.common import REQUIRED_VALUE, apply_defaults
 from pyrit.common.deprecation import print_deprecation_message  # Deprecated. Will be removed in 0.16.0.
@@ -219,9 +219,9 @@ class RedTeamAgent(Scenario):
     def __init__(
         self,
         *,
-        adversarial_chat: Optional[PromptTarget] = None,
-        attack_scoring_config: Optional[AttackScoringConfig] = None,
-        scenario_result_id: Optional[str] = None,
+        adversarial_chat: PromptTarget | None = None,
+        attack_scoring_config: AttackScoringConfig | None = None,
+        scenario_result_id: str | None = None,
         include_baseline: bool | None = None,  # Deprecated. Will be removed in 0.16.0.
     ) -> None:
         """
@@ -280,13 +280,11 @@ async def initialize_async(
         self,
         *,
         objective_target: PromptTarget = REQUIRED_VALUE,  # type: ignore[ty:invalid-parameter-default]
-        scenario_strategies: Optional[
-            Sequence["FoundryStrategy | FoundryComposite | ScenarioCompositeStrategy"]
-        ] = None,
-        dataset_config: Optional[DatasetConfiguration] = None,
+        scenario_strategies: Sequence["FoundryStrategy | FoundryComposite | ScenarioCompositeStrategy"] | None = None,
+        dataset_config: DatasetConfiguration | None = None,
         max_concurrency: int = 4,
         max_retries: int = 0,
-        memory_labels: Optional[dict[str, str]] = None,
+        memory_labels: dict[str, str] | None = None,
         include_baseline: bool | None = None,
     ) -> None:
         """
@@ -320,7 +318,7 @@ async def initialize_async(
 
     def _prepare_strategies(  # type: ignore[ty:invalid-method-override]
         self,
-        strategies: "Optional[Sequence[FoundryStrategy | FoundryComposite | ScenarioCompositeStrategy]]",
+        strategies: "Sequence[FoundryStrategy | FoundryComposite | ScenarioCompositeStrategy] | None",
     ) -> list[ScenarioStrategy]:
         """
         Resolve strategies and build FoundryComposite objects.
@@ -510,7 +508,7 @@ def _get_attack(
         *,
         attack_type: type[AttackStrategyT],
         converters: list[PromptConverter],
-        attack_kwargs: Optional[dict[str, Any]] = None,
+        attack_kwargs: dict[str, Any] | None = None,
     ) -> AttackStrategyT:
         """
         Create an attack instance with the specified converters.
diff --git a/pyrit/scenario/scenarios/garak/encoding.py b/pyrit/scenario/scenarios/garak/encoding.py
index 65f36e3218..5e8674ea0d 100644
--- a/pyrit/scenario/scenarios/garak/encoding.py
+++ b/pyrit/scenario/scenarios/garak/encoding.py
@@ -4,7 +4,6 @@
 
 import logging
 from collections.abc import Sequence
-from typing import Optional
 
 from pyrit.common import apply_defaults
 from pyrit.common.deprecation import print_deprecation_message  # Deprecated. Will be removed in 0.16.0.
@@ -138,9 +137,9 @@ class Encoding(Scenario):
     def __init__(
         self,
         *,
-        objective_scorer: Optional[TrueFalseScorer] = None,
-        encoding_templates: Optional[Sequence[str]] = None,
-        scenario_result_id: Optional[str] = None,
+        objective_scorer: TrueFalseScorer | None = None,
+        encoding_templates: Sequence[str] | None = None,
+        scenario_result_id: str | None = None,
         include_baseline: bool | None = None,  # Deprecated. Will be removed in 0.16.0.
     ) -> None:
         """
@@ -184,7 +183,7 @@ def __init__(
             self._legacy_include_baseline = include_baseline
 
         # Will be resolved in _get_atomic_attacks_async
-        self._resolved_seed_groups: Optional[list[SeedAttackGroup]] = None
+        self._resolved_seed_groups: list[SeedAttackGroup] | None = None
 
     def _resolve_seed_groups(self) -> list[SeedAttackGroup]:
         """
diff --git a/pyrit/score/audio_transcript_scorer.py b/pyrit/score/audio_transcript_scorer.py
index eb9cc87454..13764d4f61 100644
--- a/pyrit/score/audio_transcript_scorer.py
+++ b/pyrit/score/audio_transcript_scorer.py
@@ -6,7 +6,6 @@
 import tempfile
 import uuid
 from pathlib import Path
-from typing import Optional
 
 import av
 
@@ -107,7 +106,7 @@ def __init__(
         self,
         *,
         text_capable_scorer: Scorer,
-        use_entra_auth: Optional[bool] = None,
+        use_entra_auth: bool | None = None,
     ) -> None:
         """
         Initialize the base audio scorer.
@@ -154,7 +153,7 @@ def _validate_text_scorer(scorer: Scorer) -> None:
                 f"Supported types: {scorer._validator._supported_data_types}"
             )
 
-    async def _score_audio_async(self, *, message_piece: MessagePiece, objective: Optional[str] = None) -> list[Score]:
+    async def _score_audio_async(self, *, message_piece: MessagePiece, objective: str | None = None) -> list[Score]:
         """
         Transcribe audio and score the transcript.
 
@@ -267,7 +266,7 @@ def _ensure_wav_format(self, audio_path: str) -> str:
             channels=self._DEFAULT_CHANNELS,
         )
 
-    def _extract_audio_from_video(self, video_path: str) -> Optional[str]:
+    def _extract_audio_from_video(self, video_path: str) -> str | None:
         """
         Extract audio track from a video file.
 
@@ -281,7 +280,7 @@ def _extract_audio_from_video(self, video_path: str) -> Optional[str]:
         return AudioTranscriptHelper.extract_audio_from_video(video_path)
 
     @staticmethod
-    def extract_audio_from_video(video_path: str) -> Optional[str]:
+    def extract_audio_from_video(video_path: str) -> str | None:
         """
         Extract audio track from a video file (static version).
 
diff --git a/pyrit/score/batch_scorer.py b/pyrit/score/batch_scorer.py
index 66beec5261..2c9d993540 100644
--- a/pyrit/score/batch_scorer.py
+++ b/pyrit/score/batch_scorer.py
@@ -5,7 +5,6 @@
 import uuid
 from collections.abc import Sequence
 from datetime import datetime
-from typing import Optional
 
 from pyrit.memory import CentralMemory
 from pyrit.models import (
@@ -47,17 +46,17 @@ async def score_responses_by_filters_async(
         self,
         *,
         scorer: Scorer,
-        attack_id: Optional[str | uuid.UUID] = None,
-        conversation_id: Optional[str | uuid.UUID] = None,
-        prompt_ids: Optional[list[str] | list[uuid.UUID]] = None,
-        labels: Optional[dict[str, str]] = None,
-        sent_after: Optional[datetime] = None,
-        sent_before: Optional[datetime] = None,
-        original_values: Optional[list[str]] = None,
-        converted_values: Optional[list[str]] = None,
-        data_type: Optional[str] = None,
-        not_data_type: Optional[str] = None,
-        converted_value_sha256: Optional[list[str]] = None,
+        attack_id: str | uuid.UUID | None = None,
+        conversation_id: str | uuid.UUID | None = None,
+        prompt_ids: list[str] | list[uuid.UUID] | None = None,
+        labels: dict[str, str] | None = None,
+        sent_after: datetime | None = None,
+        sent_before: datetime | None = None,
+        original_values: list[str] | None = None,
+        converted_values: list[str] | None = None,
+        data_type: str | None = None,
+        not_data_type: str | None = None,
+        converted_value_sha256: list[str] | None = None,
         objective: str = "",
     ) -> list[Score]:
         """
diff --git a/pyrit/score/conversation_scorer.py b/pyrit/score/conversation_scorer.py
index d4e824d1fe..57385e6f1d 100644
--- a/pyrit/score/conversation_scorer.py
+++ b/pyrit/score/conversation_scorer.py
@@ -3,7 +3,7 @@
 
 import uuid
 from abc import ABC, abstractmethod
-from typing import Optional, cast
+from typing import cast
 from uuid import UUID
 
 from pyrit.models import ComponentIdentifier, Message, MessagePiece, Score
@@ -32,7 +32,7 @@ class ConversationScorer(Scorer, ABC):
         enforce_all_pieces_valid=False,
     )
 
-    async def _score_async(self, message: Message, *, objective: Optional[str] = None) -> list[Score]:
+    async def _score_async(self, message: Message, *, objective: str | None = None) -> list[Score]:
         """
         Scores the entire conversation history by concatenating all messages and passing to the wrapped scorer.
 
@@ -128,7 +128,7 @@ async def _score_async(self, message: Message, *, objective: Optional[str] = Non
 
         return scores
 
-    async def _score_piece_async(self, message_piece: MessagePiece, *, objective: Optional[str] = None) -> list[Score]:
+    async def _score_piece_async(self, message_piece: MessagePiece, *, objective: str | None = None) -> list[Score]:
         """
         Not used - ConversationScorer operates at conversation level via _score_async.
 
@@ -159,7 +159,7 @@ def validate_return_scores(self, scores: list[Score]) -> None:
 def create_conversation_scorer(
     *,
     scorer: Scorer,
-    validator: Optional[ScorerPromptValidator] = None,
+    validator: ScorerPromptValidator | None = None,
 ) -> Scorer:
     """
     Create a ConversationScorer that inherits from the same type as the wrapped scorer.
@@ -187,7 +187,7 @@ def create_conversation_scorer(
         >>> isinstance(conversation_scorer, ConversationScorer)  # True
     """
     # Determine the base class of the wrapped scorer
-    scorer_base_class: Optional[type[Scorer]] = None
+    scorer_base_class: type[Scorer] | None = None
 
     if isinstance(scorer, FloatScaleScorer):
         scorer_base_class = FloatScaleScorer
diff --git a/pyrit/score/float_scale/audio_float_scale_scorer.py b/pyrit/score/float_scale/audio_float_scale_scorer.py
index 203f8e1281..17653c9d5f 100644
--- a/pyrit/score/float_scale/audio_float_scale_scorer.py
+++ b/pyrit/score/float_scale/audio_float_scale_scorer.py
@@ -1,7 +1,6 @@
 # Copyright (c) Microsoft Corporation.
 # Licensed under the MIT license.
 
-from typing import Optional
 
 from pyrit.models import ComponentIdentifier, MessagePiece, Score
 from pyrit.score.audio_transcript_scorer import AudioTranscriptHelper
@@ -23,8 +22,8 @@ def __init__(
         self,
         *,
         text_capable_scorer: FloatScaleScorer,
-        validator: Optional[ScorerPromptValidator] = None,
-        use_entra_auth: Optional[bool] = None,
+        validator: ScorerPromptValidator | None = None,
+        use_entra_auth: bool | None = None,
     ) -> None:
         """
         Initialize the AudioFloatScaleScorer.
@@ -62,7 +61,7 @@ def _build_identifier(self) -> ComponentIdentifier:
             },
         )
 
-    async def _score_piece_async(self, message_piece: MessagePiece, *, objective: Optional[str] = None) -> list[Score]:
+    async def _score_piece_async(self, message_piece: MessagePiece, *, objective: str | None = None) -> list[Score]:
         """
         Score an audio file by transcribing it and scoring the transcript.
 
diff --git a/pyrit/score/float_scale/azure_content_filter_scorer.py b/pyrit/score/float_scale/azure_content_filter_scorer.py
index 2ef3b412fb..85658563de 100644
--- a/pyrit/score/float_scale/azure_content_filter_scorer.py
+++ b/pyrit/score/float_scale/azure_content_filter_scorer.py
@@ -95,10 +95,10 @@ def _get_eval_files_for_category(cls, category: TextCategory) -> Optional["Score
     def __init__(
         self,
         *,
-        endpoint: Optional[str | None] = None,
-        api_key: Optional[str | Callable[[], str | Awaitable[str]] | None] = None,
-        harm_categories: Optional[list[TextCategory]] = None,
-        validator: Optional[ScorerPromptValidator] = None,
+        endpoint: str | None = None,
+        api_key: str | Callable[[], str | Awaitable[str]] | None = None,
+        harm_categories: list[TextCategory] | None = None,
+        validator: ScorerPromptValidator | None = None,
     ) -> None:
         """
         Initialize an Azure Content Filter Scorer.
@@ -247,7 +247,7 @@ def _get_chunks(self, text: str) -> list[str]:
 
         return [text[i : i + self.MAX_TEXT_LENGTH] for i in range(0, len(text), self.MAX_TEXT_LENGTH)]
 
-    async def _score_piece_async(self, message_piece: MessagePiece, *, objective: Optional[str] = None) -> list[Score]:
+    async def _score_piece_async(self, message_piece: MessagePiece, *, objective: str | None = None) -> list[Score]:
         """
         Evaluate the input text or image using the Azure Content Filter API.
 
@@ -343,7 +343,7 @@ async def _score_piece_async(self, message_piece: MessagePiece, *, objective: Op
             for result in aggregated_results
         ]
 
-    def _build_fallback_score(self, *, message: Message, objective: Optional[str]) -> list[Score]:
+    def _build_fallback_score(self, *, message: Message, objective: str | None) -> list[Score]:
         """
         Build one neutral ``0.0`` fallback score per configured harm category.
 
diff --git a/pyrit/score/float_scale/float_scale_scorer.py b/pyrit/score/float_scale/float_scale_scorer.py
index c888c117f3..6d1f9ab3e5 100644
--- a/pyrit/score/float_scale/float_scale_scorer.py
+++ b/pyrit/score/float_scale/float_scale_scorer.py
@@ -35,7 +35,7 @@ class FloatScaleScorer(Scorer):
     "blocked = True") should override ``_score_piece_async`` or ``_build_fallback_score``.
     """
 
-    def __init__(self, *, validator: ScorerPromptValidator, chat_target: Optional[PromptTarget] = None) -> None:
+    def __init__(self, *, validator: ScorerPromptValidator, chat_target: PromptTarget | None = None) -> None:
         """
         Initialize the FloatScaleScorer.
 
@@ -46,7 +46,7 @@ def __init__(self, *, validator: ScorerPromptValidator, chat_target: Optional[Pr
         """
         super().__init__(validator=validator, chat_target=chat_target)
 
-    def _build_fallback_score(self, *, message: Message, objective: Optional[str]) -> list[Score]:
+    def _build_fallback_score(self, *, message: Message, objective: str | None) -> list[Score]:
         """
         Build a single-element list containing a neutral ``0.0`` score when no pieces could be scored.
 
@@ -138,15 +138,15 @@ async def _score_value_with_llm_async(
         message_value: str,
         message_data_type: PromptDataType,
         scored_prompt_id: str | UUID,
-        prepended_text_message_piece: Optional[str] = None,
-        category: Optional[str | UUID] = None,
-        objective: Optional[str] = None,
+        prepended_text_message_piece: str | None = None,
+        category: str | UUID | None = None,
+        objective: str | None = None,
         score_value_output_key: str = "score_value",
         rationale_output_key: str = "rationale",
         description_output_key: str = "description",
         metadata_output_key: str = "metadata",
         category_output_key: str = "category",
-        attack_identifier: Optional[ComponentIdentifier] = None,
+        attack_identifier: ComponentIdentifier | None = None,
     ) -> UnvalidatedScore:
         score: UnvalidatedScore | None = None
         try:
diff --git a/pyrit/score/float_scale/insecure_code_scorer.py b/pyrit/score/float_scale/insecure_code_scorer.py
index 91d795e9e4..128b536a10 100644
--- a/pyrit/score/float_scale/insecure_code_scorer.py
+++ b/pyrit/score/float_scale/insecure_code_scorer.py
@@ -2,7 +2,6 @@
 # Licensed under the MIT license.
 
 from pathlib import Path
-from typing import Optional, Union
 
 from pyrit.common import verify_and_resolve_path
 from pyrit.common.path import SCORER_SEED_PROMPT_PATH
@@ -26,8 +25,8 @@ def __init__(
         self,
         *,
         chat_target: PromptTarget,
-        system_prompt_path: Optional[Union[str, Path]] = None,
-        validator: Optional[ScorerPromptValidator] = None,
+        system_prompt_path: str | Path | None = None,
+        validator: ScorerPromptValidator | None = None,
     ) -> None:
         """
         Initialize the Insecure Code Scorer.
@@ -72,7 +71,7 @@ def _build_identifier(self) -> ComponentIdentifier:
             },
         )
 
-    async def _score_piece_async(self, message_piece: MessagePiece, *, objective: Optional[str] = None) -> list[Score]:
+    async def _score_piece_async(self, message_piece: MessagePiece, *, objective: str | None = None) -> list[Score]:
         """
         Scores the given message piece using LLM to detect security vulnerabilities.
 
diff --git a/pyrit/score/float_scale/plagiarism_scorer.py b/pyrit/score/float_scale/plagiarism_scorer.py
index 3547767114..e608f79ca4 100644
--- a/pyrit/score/float_scale/plagiarism_scorer.py
+++ b/pyrit/score/float_scale/plagiarism_scorer.py
@@ -3,7 +3,6 @@
 
 import re
 from enum import Enum
-from typing import Optional
 
 import numpy as np
 
@@ -38,7 +37,7 @@ def __init__(
         reference_text: str,
         metric: PlagiarismMetric = PlagiarismMetric.LCS,
         n: int = 5,
-        validator: Optional[ScorerPromptValidator] = None,
+        validator: ScorerPromptValidator | None = None,
     ) -> None:
         """
         Initialize the PlagiarismScorer.
@@ -164,7 +163,7 @@ def _plagiarism_score(
 
         raise ValueError("metric must be 'lcs', 'levenshtein', or 'jaccard'")
 
-    async def _score_piece_async(self, message_piece: MessagePiece, *, objective: Optional[str] = None) -> list[Score]:
+    async def _score_piece_async(self, message_piece: MessagePiece, *, objective: str | None = None) -> list[Score]:
         """
         Scores the AI response against the reference text using the specified metric.
 
diff --git a/pyrit/score/float_scale/self_ask_general_float_scale_scorer.py b/pyrit/score/float_scale/self_ask_general_float_scale_scorer.py
index fa1b56627d..9e5d8bd3a4 100644
--- a/pyrit/score/float_scale/self_ask_general_float_scale_scorer.py
+++ b/pyrit/score/float_scale/self_ask_general_float_scale_scorer.py
@@ -3,7 +3,7 @@
 
 from __future__ import annotations
 
-from typing import TYPE_CHECKING, Optional
+from typing import TYPE_CHECKING
 
 from pyrit.prompt_target import CHAT_TARGET_REQUIREMENTS
 from pyrit.score.float_scale.float_scale_scorer import FloatScaleScorer
@@ -31,11 +31,11 @@ def __init__(
         *,
         chat_target: PromptTarget,
         system_prompt_format_string: str,
-        prompt_format_string: Optional[str] = None,
-        category: Optional[str] = None,
+        prompt_format_string: str | None = None,
+        category: str | None = None,
         min_value: int = 0,
         max_value: int = 100,
-        validator: Optional[ScorerPromptValidator] = None,
+        validator: ScorerPromptValidator | None = None,
         score_value_output_key: str = "score_value",
         rationale_output_key: str = "rationale",
         description_output_key: str = "description",
@@ -112,7 +112,7 @@ def _build_identifier(self) -> ComponentIdentifier:
             },
         )
 
-    async def _score_piece_async(self, message_piece: MessagePiece, *, objective: Optional[str] = None) -> list[Score]:
+    async def _score_piece_async(self, message_piece: MessagePiece, *, objective: str | None = None) -> list[Score]:
         """
         Score a single message piece using the configured prompts and scale to [0, 1].
 
diff --git a/pyrit/score/float_scale/self_ask_likert_scorer.py b/pyrit/score/float_scale/self_ask_likert_scorer.py
index 6134f6f7af..15c496dd6c 100644
--- a/pyrit/score/float_scale/self_ask_likert_scorer.py
+++ b/pyrit/score/float_scale/self_ask_likert_scorer.py
@@ -5,7 +5,6 @@
 import logging
 from dataclasses import dataclass
 from pathlib import Path
-from typing import Optional
 
 import yaml
 
@@ -32,7 +31,7 @@ class LikertScaleEvalFiles:
 
     human_labeled_datasets_files: list[str]
     result_file: str
-    harm_category: Optional[str] = None
+    harm_category: str | None = None
 
 
 class LikertScalePaths(enum.Enum):
@@ -158,7 +157,7 @@ def path(self) -> Path:
         return self.value[0]
 
     @property
-    def evaluation_files(self) -> Optional[LikertScaleEvalFiles]:
+    def evaluation_files(self) -> LikertScaleEvalFiles | None:
         """Get the evaluation file configuration, or None if no evaluation dataset exists."""
         return self.value[1]
 
@@ -178,10 +177,10 @@ def __init__(
         self,
         *,
         chat_target: PromptTarget,
-        likert_scale: Optional[LikertScalePaths] = None,
-        custom_likert_path: Optional[Path] = None,
-        custom_system_prompt_path: Optional[Path] = None,
-        validator: Optional[ScorerPromptValidator] = None,
+        likert_scale: LikertScalePaths | None = None,
+        custom_likert_path: Path | None = None,
+        custom_system_prompt_path: Path | None = None,
+        validator: ScorerPromptValidator | None = None,
     ) -> None:
         """
         Initialize the SelfAskLikertScorer.
@@ -211,9 +210,7 @@ def __init__(
         if likert_scale is None and custom_likert_path is None:
             raise ValueError("One of 'likert_scale' or 'custom_likert_path' must be provided.")
 
-        self._scoring_instructions_template: Optional[SeedPrompt] = (
-            None  # Will be set in _set_likert_scale_system_prompt
-        )
+        self._scoring_instructions_template: SeedPrompt | None = None  # Will be set in _set_likert_scale_system_prompt
         if custom_system_prompt_path is not None:
             self._validate_custom_system_prompt_path(custom_system_prompt_path)
             self._scoring_instructions_template = SeedPrompt.from_yaml_file(custom_system_prompt_path)
@@ -436,7 +433,7 @@ def _validate_custom_likert_path(custom_likert_path: Path) -> None:
                 f"Custom Likert scale file must be a YAML file (.yaml or .yml), got '{custom_likert_path.suffix}'."
             )
 
-    async def _score_piece_async(self, message_piece: MessagePiece, *, objective: Optional[str] = None) -> list[Score]:
+    async def _score_piece_async(self, message_piece: MessagePiece, *, objective: str | None = None) -> list[Score]:
         """
         Score the given message_piece using "self-ask" for the chat target.
 
diff --git a/pyrit/score/float_scale/self_ask_scale_scorer.py b/pyrit/score/float_scale/self_ask_scale_scorer.py
index 6cdc1e2921..992d403ca7 100644
--- a/pyrit/score/float_scale/self_ask_scale_scorer.py
+++ b/pyrit/score/float_scale/self_ask_scale_scorer.py
@@ -3,7 +3,7 @@
 
 import enum
 from pathlib import Path
-from typing import Any, Optional, Union
+from typing import Any
 
 import yaml
 
@@ -44,9 +44,9 @@ def __init__(
         self,
         *,
         chat_target: PromptTarget,
-        scale_arguments_path: Optional[Union[Path, str]] = None,
-        system_prompt_path: Optional[Union[Path, str]] = None,
-        validator: Optional[ScorerPromptValidator] = None,
+        scale_arguments_path: Path | str | None = None,
+        system_prompt_path: Path | str | None = None,
+        validator: ScorerPromptValidator | None = None,
     ) -> None:
         """
         Initialize the SelfAskScaleScorer.
@@ -101,7 +101,7 @@ def _build_identifier(self) -> ComponentIdentifier:
             },
         )
 
-    async def _score_piece_async(self, message_piece: MessagePiece, *, objective: Optional[str] = None) -> list[Score]:
+    async def _score_piece_async(self, message_piece: MessagePiece, *, objective: str | None = None) -> list[Score]:
         """
         Scores the given message_piece using "self-ask" for the chat target.
 
diff --git a/pyrit/score/float_scale/video_float_scale_scorer.py b/pyrit/score/float_scale/video_float_scale_scorer.py
index cb337aa506..9845bb34ac 100644
--- a/pyrit/score/float_scale/video_float_scale_scorer.py
+++ b/pyrit/score/float_scale/video_float_scale_scorer.py
@@ -1,7 +1,7 @@
 # Copyright (c) Microsoft Corporation.
 # Licensed under the MIT license.
 
-from typing import TYPE_CHECKING, Optional
+from typing import TYPE_CHECKING
 
 from pyrit.models import ComponentIdentifier, MessagePiece, Score
 from pyrit.score.float_scale.float_scale_score_aggregator import (
@@ -42,12 +42,12 @@ def __init__(
         self,
         *,
         image_capable_scorer: FloatScaleScorer,
-        audio_scorer: Optional[FloatScaleScorer] = None,
-        num_sampled_frames: Optional[int] = None,
-        validator: Optional[ScorerPromptValidator] = None,
+        audio_scorer: FloatScaleScorer | None = None,
+        num_sampled_frames: int | None = None,
+        validator: ScorerPromptValidator | None = None,
         score_aggregator: FloatScaleAggregatorFunc = FloatScaleScorerByCategory.MAX,
-        image_objective_template: Optional[str] = VideoHelper._DEFAULT_IMAGE_OBJECTIVE_TEMPLATE,
-        audio_objective_template: Optional[str] = None,
+        image_objective_template: str | None = VideoHelper._DEFAULT_IMAGE_OBJECTIVE_TEMPLATE,
+        audio_objective_template: str | None = None,
     ) -> None:
         """
         Initialize the VideoFloatScaleScorer.
@@ -116,7 +116,7 @@ def _build_identifier(self) -> ComponentIdentifier:
             },
         )
 
-    async def _score_piece_async(self, message_piece: MessagePiece, *, objective: Optional[str] = None) -> list[Score]:
+    async def _score_piece_async(self, message_piece: MessagePiece, *, objective: str | None = None) -> list[Score]:
         """
         Score a single video piece by extracting frames and optionally audio, then aggregating their scores.
 
diff --git a/pyrit/score/score_aggregator_result.py b/pyrit/score/score_aggregator_result.py
index de5b8dc212..84133eb27a 100644
--- a/pyrit/score/score_aggregator_result.py
+++ b/pyrit/score/score_aggregator_result.py
@@ -2,7 +2,6 @@
 # Licensed under the MIT license.
 
 from dataclasses import dataclass
-from typing import Union
 
 
 @dataclass(frozen=True, slots=True)
@@ -19,8 +18,8 @@ class ScoreAggregatorResult:
         metadata (Dict[str, Union[str, int, float]]): Combined metadata from constituent scores.
     """
 
-    value: Union[bool, float]
+    value: bool | float
     description: str
     rationale: str
     category: list[str]
-    metadata: dict[str, Union[str, int, float]]
+    metadata: dict[str, str | int | float]
diff --git a/pyrit/score/score_utils.py b/pyrit/score/score_utils.py
index 5ae68c3939..4429b34e67 100644
--- a/pyrit/score/score_utils.py
+++ b/pyrit/score/score_utils.py
@@ -1,7 +1,6 @@
 # Copyright (c) Microsoft Corporation.
 # Licensed under the MIT license.
 
-from typing import Optional, Union
 
 from pyrit.common.utils import combine_dict
 from pyrit.models import Score
@@ -11,7 +10,7 @@
 ORIGINAL_FLOAT_VALUE_KEY = "original_float_value"
 
 
-def combine_metadata_and_categories(scores: list[Score]) -> tuple[dict[str, Union[str, int, float]], list[str]]:
+def combine_metadata_and_categories(scores: list[Score]) -> tuple[dict[str, str | int | float], list[str]]:
     """
     Combine metadata and categories from multiple scores with deduplication.
 
@@ -21,7 +20,7 @@ def combine_metadata_and_categories(scores: list[Score]) -> tuple[dict[str, Unio
     Returns:
         Tuple of (metadata dict, sorted category list with empty strings filtered).
     """
-    metadata: dict[str, Union[str, int, float]] = {}
+    metadata: dict[str, str | int | float] = {}
     category_set: set[str] = set()
 
     for s in scores:
@@ -47,7 +46,7 @@ def format_score_for_rationale(score: Score) -> str:
     return f"   - {class_type} {score.score_value}: {score.score_rationale or ''}"
 
 
-def normalize_score_to_float(score: Optional[Score]) -> float:
+def normalize_score_to_float(score: Score | None) -> float:
     """
     Normalize any score to a float value between 0.0 and 1.0.
 
diff --git a/pyrit/score/scorer.py b/pyrit/score/scorer.py
index ce133df66a..28c7d330b0 100644
--- a/pyrit/score/scorer.py
+++ b/pyrit/score/scorer.py
@@ -13,8 +13,6 @@
     TYPE_CHECKING,
     Any,
     ClassVar,
-    Optional,
-    Union,
     cast,
 )
 
@@ -61,7 +59,7 @@ class Scorer(Identifiable, abc.ABC):
 
     # Evaluation configuration - maps input dataset files to a result file.
     # Specifies glob patterns for datasets and a result file name.
-    evaluation_file_mapping: Optional[ScorerEvalDatasetFiles] = None
+    evaluation_file_mapping: ScorerEvalDatasetFiles | None = None
 
     #: Capability requirements placed on the scorer's chat target (if any).
     #: Subclasses that use a chat target should override this and pass the
@@ -69,7 +67,7 @@ class Scorer(Identifiable, abc.ABC):
     #: validate it.
     TARGET_REQUIREMENTS: ClassVar[TargetRequirements] = TargetRequirements()
 
-    _identifier: Optional[ComponentIdentifier] = None
+    _identifier: ComponentIdentifier | None = None
 
     #: When True, blocked responses that contain partial content
     #: (in prompt_metadata["partial_content"]) will be scored using that content
@@ -80,7 +78,7 @@ class Scorer(Identifiable, abc.ABC):
     #: (Chat Completions API) and ``OpenAIResponseTarget`` (Responses API).
     score_blocked_content: bool = False
 
-    def __init__(self, *, validator: ScorerPromptValidator, chat_target: Optional[PromptTarget] = None) -> None:
+    def __init__(self, *, validator: ScorerPromptValidator, chat_target: PromptTarget | None = None) -> None:
         """
         Initialize the Scorer.
 
@@ -148,8 +146,8 @@ def _memory(self) -> MemoryInterface:
     def _create_identifier(
         self,
         *,
-        params: Optional[dict[str, Any]] = None,
-        children: Optional[dict[str, Union[ComponentIdentifier, list[ComponentIdentifier]]]] = None,
+        params: dict[str, Any] | None = None,
+        children: dict[str, ComponentIdentifier | list[ComponentIdentifier]] | None = None,
     ) -> ComponentIdentifier:
         """
         Construct the scorer identifier.
@@ -182,8 +180,8 @@ async def score_async(
         self,
         message: Message,
         *,
-        objective: Optional[str] = None,
-        role_filter: Optional[ChatMessageRole] = None,
+        objective: str | None = None,
+        role_filter: ChatMessageRole | None = None,
         skip_on_error_result: bool = False,
         infer_objective_from_request: bool = False,
     ) -> list[Score]:
@@ -266,7 +264,7 @@ async def score_async(
 
         return scores
 
-    async def _score_async(self, message: Message, *, objective: Optional[str] = None) -> list[Score]:
+    async def _score_async(self, message: Message, *, objective: str | None = None) -> list[Score]:
         """
         Score the given request response asynchronously.
 
@@ -299,11 +297,11 @@ async def _score_async(self, message: Message, *, objective: Optional[str] = Non
         return [score for sublist in piece_score_lists for score in sublist]
 
     @abstractmethod
-    async def _score_piece_async(self, message_piece: MessagePiece, *, objective: Optional[str] = None) -> list[Score]:
+    async def _score_piece_async(self, message_piece: MessagePiece, *, objective: str | None = None) -> list[Score]:
         raise NotImplementedError
 
     @staticmethod
-    def _create_text_piece_from_blocked(piece: MessagePiece) -> Optional[MessagePiece]:
+    def _create_text_piece_from_blocked(piece: MessagePiece) -> MessagePiece | None:
         """
         Create a text-typed copy of a blocked MessagePiece using its partial content.
 
@@ -382,7 +380,7 @@ def _get_supported_pieces(self, message: Message) -> list[MessagePiece]:
         ]
 
     @abstractmethod
-    def _build_fallback_score(self, *, message: Message, objective: Optional[str]) -> list[Score]:
+    def _build_fallback_score(self, *, message: Message, objective: str | None) -> list[Score]:
         """
         Return neutral fallback ``Score`` objects when ``_score_async`` produced no scores.
 
@@ -420,12 +418,12 @@ def validate_return_scores(self, scores: list[Score]) -> None:
 
     async def evaluate_async(
         self,
-        file_mapping: Optional[ScorerEvalDatasetFiles] = None,
+        file_mapping: ScorerEvalDatasetFiles | None = None,
         *,
         num_scorer_trials: int = 3,
         update_registry_behavior: RegistryUpdateBehavior | None = None,
         max_concurrency: int = 10,
-    ) -> Optional[ScorerMetrics]:
+    ) -> ScorerMetrics | None:
         """
         Evaluate this scorer against human-labeled datasets.
 
@@ -474,7 +472,7 @@ async def evaluate_async(
         )
 
     @abstractmethod
-    def get_scorer_metrics(self) -> Optional[ScorerMetrics]:
+    def get_scorer_metrics(self) -> ScorerMetrics | None:
         """
         Get evaluation metrics for this scorer from the configured evaluation result file.
 
@@ -490,7 +488,7 @@ def get_scorer_metrics(self) -> Optional[ScorerMetrics]:
         """
         raise NotImplementedError("Subclasses must implement get_scorer_metrics")
 
-    async def score_text_async(self, text: str, *, objective: Optional[str] = None) -> list[Score]:
+    async def score_text_async(self, text: str, *, objective: str | None = None) -> list[Score]:
         """
         Scores the given text based on the task using the chat target.
 
@@ -513,7 +511,7 @@ async def score_text_async(self, text: str, *, objective: Optional[str] = None)
         request.message_pieces[0].not_in_memory = True
         return await self.score_async(request, objective=objective)
 
-    async def score_image_async(self, image_path: str, *, objective: Optional[str] = None) -> list[Score]:
+    async def score_image_async(self, image_path: str, *, objective: str | None = None) -> list[Score]:
         """
         Score the given image using the chat target.
 
@@ -541,9 +539,9 @@ async def score_prompts_batch_async(
         self,
         *,
         messages: Sequence[Message],
-        objectives: Optional[Sequence[str]] = None,
+        objectives: Sequence[str] | None = None,
         batch_size: int = 10,
-        role_filter: Optional[ChatMessageRole] = None,
+        role_filter: ChatMessageRole | None = None,
         skip_on_error_result: bool = False,
         infer_objective_from_request: bool = False,
     ) -> list[Score]:
@@ -593,7 +591,7 @@ async def score_prompts_batch_async(
         return [score for sublist in results for score in sublist]
 
     async def score_image_batch_async(
-        self, *, image_paths: Sequence[str], objectives: Optional[Sequence[str]] = None, batch_size: int = 10
+        self, *, image_paths: Sequence[str], objectives: Sequence[str] | None = None, batch_size: int = 10
     ) -> list[Score]:
         """
         Score a batch of images asynchronously.
@@ -653,15 +651,15 @@ async def _score_value_with_llm_async(
         message_value: str,
         message_data_type: PromptDataType,
         scored_prompt_id: str,
-        prepended_text_message_piece: Optional[str] = None,
-        category: Optional[Sequence[str] | str] = None,
-        objective: Optional[str] = None,
+        prepended_text_message_piece: str | None = None,
+        category: Sequence[str] | str | None = None,
+        objective: str | None = None,
         score_value_output_key: str = "score_value",
         rationale_output_key: str = "rationale",
         description_output_key: str = "description",
         metadata_output_key: str = "metadata",
         category_output_key: str = "category",
-        attack_identifier: Optional[ComponentIdentifier] = None,
+        attack_identifier: ComponentIdentifier | None = None,
     ) -> UnvalidatedScore:
         """
         Send a request to a target, and take care of retries.
@@ -769,7 +767,7 @@ async def _score_value_with_llm_async(
 
             # Validate and normalize category to a list of strings
             cat_val = category_response if category_response is not None else category
-            normalized_category: Optional[list[str]]
+            normalized_category: list[str] | None
             if cat_val is None:
                 normalized_category = None
             elif isinstance(cat_val, str):
@@ -784,7 +782,7 @@ async def _score_value_with_llm_async(
 
             # Normalize metadata to a dictionary with string keys and string/int/float values
             raw_md = parsed_response.get(metadata_output_key)
-            normalized_md: Optional[dict[str, Union[str, int, float]]]
+            normalized_md: dict[str, str | int | float] | None
             if raw_md is None:
                 normalized_md = None
             elif isinstance(raw_md, dict):
@@ -851,10 +849,10 @@ def _extract_objective_from_response(self, response: Message) -> str:
     async def score_response_async(
         *,
         response: Message,
-        objective_scorer: Optional[Scorer] = None,
-        auxiliary_scorers: Optional[list[Scorer]] = None,
+        objective_scorer: Scorer | None = None,
+        auxiliary_scorers: list[Scorer] | None = None,
         role_filter: ChatMessageRole = "assistant",
-        objective: Optional[str] = None,
+        objective: str | None = None,
         skip_on_error_result: bool = True,
     ) -> dict[str, list[Score]]:
         """
@@ -929,7 +927,7 @@ async def score_response_multiple_scorers_async(
         response: Message,
         scorers: list[Scorer],
         role_filter: ChatMessageRole = "assistant",
-        objective: Optional[str] = None,
+        objective: str | None = None,
         skip_on_error_result: bool = True,
     ) -> list[Score]:
         """
diff --git a/pyrit/score/scorer_evaluation/human_labeled_dataset.py b/pyrit/score/scorer_evaluation/human_labeled_dataset.py
index f0f0fdcd87..635d9daf2f 100644
--- a/pyrit/score/scorer_evaluation/human_labeled_dataset.py
+++ b/pyrit/score/scorer_evaluation/human_labeled_dataset.py
@@ -5,7 +5,7 @@
 import logging
 from dataclasses import dataclass
 from pathlib import Path
-from typing import TYPE_CHECKING, Any, Optional, Union, cast
+from typing import TYPE_CHECKING, Any, Optional, cast
 
 import pandas as pd
 
@@ -126,8 +126,8 @@ def __init__(
         entries: list[HumanLabeledEntry],
         metrics_type: MetricsType,
         version: str,
-        harm_definition: Optional[str] = None,
-        harm_definition_version: Optional[str] = None,
+        harm_definition: str | None = None,
+        harm_definition_version: str | None = None,
     ) -> None:
         """
         Initialize the HumanLabeledDataset.
@@ -156,7 +156,7 @@ def __init__(
         self.version = version
         self.harm_definition = harm_definition
         self.harm_definition_version = harm_definition_version
-        self._harm_definition_obj: Optional[HarmDefinition] = None
+        self._harm_definition_obj: HarmDefinition | None = None
 
     def get_harm_definition(self) -> Optional["HarmDefinition"]:
         """
@@ -188,12 +188,12 @@ def get_harm_definition(self) -> Optional["HarmDefinition"]:
     def from_csv(
         cls,
         *,
-        csv_path: Union[str, Path],
+        csv_path: str | Path,
         metrics_type: MetricsType,
-        dataset_name: Optional[str] = None,
-        version: Optional[str] = None,
-        harm_definition: Optional[str] = None,
-        harm_definition_version: Optional[str] = None,
+        dataset_name: str | None = None,
+        version: str | None = None,
+        harm_definition: str | None = None,
+        harm_definition_version: str | None = None,
     ) -> "HumanLabeledDataset":
         """
         Load a human-labeled dataset from a CSV file with standard column names.
diff --git a/pyrit/score/scorer_evaluation/scorer_evaluator.py b/pyrit/score/scorer_evaluation/scorer_evaluator.py
index 5f203753fc..8034babc56 100644
--- a/pyrit/score/scorer_evaluation/scorer_evaluator.py
+++ b/pyrit/score/scorer_evaluation/scorer_evaluator.py
@@ -7,7 +7,7 @@
 import logging
 import time
 from dataclasses import dataclass
-from typing import TYPE_CHECKING, Optional, cast
+from typing import TYPE_CHECKING, cast
 
 import numpy as np
 from scipy.stats import ttest_1samp
@@ -70,7 +70,7 @@ class ScorerEvalDatasetFiles:
 
     human_labeled_datasets_files: list[str]
     result_file: str
-    harm_category: Optional[str] = None
+    harm_category: str | None = None
 
 
 class ScorerEvaluator(abc.ABC):
@@ -92,7 +92,7 @@ def __init__(self, scorer: Scorer) -> None:
         self.scorer = scorer
 
     @classmethod
-    def from_scorer(cls, scorer: Scorer, metrics_type: Optional[MetricsType] = None) -> ScorerEvaluator:
+    def from_scorer(cls, scorer: Scorer, metrics_type: MetricsType | None = None) -> ScorerEvaluator:
         """
         Create a ScorerEvaluator based on the type of scoring.
 
@@ -120,7 +120,7 @@ async def run_evaluation_async(
         num_scorer_trials: int = 3,
         update_registry_behavior: RegistryUpdateBehavior = RegistryUpdateBehavior.SKIP_IF_EXISTS,
         max_concurrency: int = 10,
-    ) -> Optional[ScorerMetrics]:
+    ) -> ScorerMetrics | None:
         """
         Evaluate scorer using dataset files configuration.
 
@@ -265,11 +265,11 @@ def _should_skip_evaluation(
         self,
         *,
         dataset_version: str,
-        harm_definition_version: Optional[str] = None,
+        harm_definition_version: str | None = None,
         num_scorer_trials: int,
-        harm_category: Optional[str] = None,
+        harm_category: str | None = None,
         result_file_path: Path,
-    ) -> tuple[bool, Optional[ScorerMetrics]]:
+    ) -> tuple[bool, ScorerMetrics | None]:
         """
         Determine whether to skip evaluation based on existing registry entries.
 
@@ -302,7 +302,7 @@ def _should_skip_evaluation(
             # Determine if this is a harm or objective evaluation
             metrics_type = MetricsType.OBJECTIVE if isinstance(self.scorer, TrueFalseScorer) else MetricsType.HARM
 
-            existing: Optional[ScorerMetrics] = None
+            existing: ScorerMetrics | None = None
             if metrics_type == MetricsType.HARM:
                 if harm_category is None:
                     logger.warning("harm_category must be provided for harm scorer evaluations")
@@ -449,7 +449,7 @@ async def evaluate_dataset_async(
     def _validate_and_extract_data(
         self,
         labeled_dataset: HumanLabeledDataset,
-    ) -> tuple[list[Message], list[list[float]], Optional[list[str]]]:
+    ) -> tuple[list[Message], list[list[float]], list[str] | None]:
         """
         Validate the dataset and extract data for evaluation.
 
@@ -471,11 +471,11 @@ def _compute_metrics(
         all_human_scores: np.ndarray,
         all_model_scores: np.ndarray,
         num_scorer_trials: int,
-        dataset_name: Optional[str] = None,
-        dataset_version: Optional[str] = None,
-        harm_category: Optional[str] = None,
-        harm_definition: Optional[str] = None,
-        harm_definition_version: Optional[str] = None,
+        dataset_name: str | None = None,
+        dataset_version: str | None = None,
+        harm_category: str | None = None,
+        harm_definition: str | None = None,
+        harm_definition_version: str | None = None,
     ) -> ScorerMetrics:
         """
         Compute evaluation metrics from human and model scores.
@@ -532,7 +532,7 @@ class HarmScorerEvaluator(ScorerEvaluator):
     def _validate_and_extract_data(
         self,
         labeled_dataset: HumanLabeledDataset,
-    ) -> tuple[list[Message], list[list[float]], Optional[list[str]]]:
+    ) -> tuple[list[Message], list[list[float]], list[str] | None]:
         """
         Validate harm dataset and extract evaluation data.
 
@@ -569,11 +569,11 @@ def _compute_metrics(
         all_human_scores: np.ndarray,
         all_model_scores: np.ndarray,
         num_scorer_trials: int,
-        dataset_name: Optional[str] = None,
-        dataset_version: Optional[str] = None,
-        harm_category: Optional[str] = None,
-        harm_definition: Optional[str] = None,
-        harm_definition_version: Optional[str] = None,
+        dataset_name: str | None = None,
+        dataset_version: str | None = None,
+        harm_category: str | None = None,
+        harm_definition: str | None = None,
+        harm_definition_version: str | None = None,
     ) -> HarmScorerMetrics:
         reliability_data = np.concatenate((all_human_scores, all_model_scores))
         # Calculate the median of human scores for each response, which is considered the gold label
@@ -647,7 +647,7 @@ class ObjectiveScorerEvaluator(ScorerEvaluator):
     def _validate_and_extract_data(
         self,
         labeled_dataset: HumanLabeledDataset,
-    ) -> tuple[list[Message], list[list[float]], Optional[list[str]]]:
+    ) -> tuple[list[Message], list[list[float]], list[str] | None]:
         """
         Validate objective dataset and extract evaluation data.
 
@@ -685,11 +685,11 @@ def _compute_metrics(
         all_human_scores: np.ndarray,
         all_model_scores: np.ndarray,
         num_scorer_trials: int,
-        dataset_name: Optional[str] = None,
-        dataset_version: Optional[str] = None,
-        harm_category: Optional[str] = None,
-        harm_definition: Optional[str] = None,
-        harm_definition_version: Optional[str] = None,
+        dataset_name: str | None = None,
+        dataset_version: str | None = None,
+        harm_category: str | None = None,
+        harm_definition: str | None = None,
+        harm_definition_version: str | None = None,
     ) -> ObjectiveScorerMetrics:
         # Calculate the majority vote of human scores for each response, which is considered the gold label.
         # If the vote is split, the resulting gold score will be 0 (i.e. False). Same logic is applied to model trials.
diff --git a/pyrit/score/scorer_evaluation/scorer_metrics.py b/pyrit/score/scorer_evaluation/scorer_metrics.py
index fab1f9a505..87546f4af1 100644
--- a/pyrit/score/scorer_evaluation/scorer_metrics.py
+++ b/pyrit/score/scorer_evaluation/scorer_metrics.py
@@ -5,7 +5,7 @@
 
 import json
 from dataclasses import asdict, dataclass, field
-from typing import TYPE_CHECKING, Generic, Optional, TypeVar, Union
+from typing import TYPE_CHECKING, Generic, TypeVar
 
 from pyrit.common.utils import verify_and_resolve_path
 
@@ -43,9 +43,9 @@ class ScorerMetrics:
     num_responses: int
     num_human_raters: int
     num_scorer_trials: int = field(default=1, kw_only=True)
-    dataset_name: Optional[str] = field(default=None, kw_only=True)
-    dataset_version: Optional[str] = field(default=None, kw_only=True)
-    trial_scores: Optional[np.ndarray] = field(default=None, kw_only=True)
+    dataset_name: str | None = field(default=None, kw_only=True)
+    dataset_version: str | None = field(default=None, kw_only=True)
+    trial_scores: np.ndarray | None = field(default=None, kw_only=True)
     average_score_time_seconds: float = field(default=0.0, kw_only=True)
 
     def to_json(self) -> str:
@@ -63,7 +63,7 @@ def to_json(self) -> str:
         return json.dumps(asdict(self))
 
     @classmethod
-    def from_json_file(cls: type[T], file_path: Union[str, Path]) -> T:
+    def from_json_file(cls: type[T], file_path: str | Path) -> T:
         """
         Load a metrics instance from a JSON file on disk.
 
@@ -96,7 +96,7 @@ def from_json_file(cls: type[T], file_path: Union[str, Path]) -> T:
         return cls(**filtered_data)
 
     @classmethod
-    def from_json(cls: type[T], file_path: Union[str, Path]) -> T:
+    def from_json(cls: type[T], file_path: str | Path) -> T:
         """
         Load a metrics instance from a JSON file (deprecated alias for ``from_json_file``).
 
@@ -157,14 +157,14 @@ class HarmScorerMetrics(ScorerMetrics):
     t_statistic: float
     p_value: float
     krippendorff_alpha_combined: float
-    harm_category: Optional[str] = field(default=None, kw_only=True)
-    harm_definition: Optional[str] = field(default=None, kw_only=True)
-    harm_definition_version: Optional[str] = field(default=None, kw_only=True)
-    krippendorff_alpha_humans: Optional[float] = None
-    krippendorff_alpha_model: Optional[float] = None
-    _harm_definition_obj: Optional[HarmDefinition] = field(default=None, init=False, repr=False)
-
-    def get_harm_definition(self) -> Optional[HarmDefinition]:
+    harm_category: str | None = field(default=None, kw_only=True)
+    harm_definition: str | None = field(default=None, kw_only=True)
+    harm_definition_version: str | None = field(default=None, kw_only=True)
+    krippendorff_alpha_humans: float | None = None
+    krippendorff_alpha_model: float | None = None
+    _harm_definition_obj: HarmDefinition | None = field(default=None, init=False, repr=False)
+
+    def get_harm_definition(self) -> HarmDefinition | None:
         """
         Load and return the HarmDefinition object for this metrics instance.
 
diff --git a/pyrit/score/scorer_evaluation/scorer_metrics_io.py b/pyrit/score/scorer_evaluation/scorer_metrics_io.py
index d915dc24ab..080d6b45e6 100644
--- a/pyrit/score/scorer_evaluation/scorer_metrics_io.py
+++ b/pyrit/score/scorer_evaluation/scorer_metrics_io.py
@@ -11,7 +11,7 @@
 import threading
 from dataclasses import asdict
 from pathlib import Path
-from typing import Any, Optional, TypeVar
+from typing import Any, TypeVar
 
 from pyrit.common.path import (
     SCORER_EVALS_PATH,
@@ -53,7 +53,7 @@ def _metrics_to_registry_dict(metrics: ScorerMetrics) -> dict[str, Any]:
 
 
 def get_all_objective_metrics(
-    file_path: Optional[Path] = None,
+    file_path: Path | None = None,
 ) -> list[ScorerMetricsWithIdentity[ObjectiveScorerMetrics]]:
     """
     Load all objective scorer metrics with full scorer identity for comparison.
@@ -151,8 +151,8 @@ def _load_metrics_from_file(
 def find_objective_metrics_by_eval_hash(
     *,
     eval_hash: str,
-    file_path: Optional[Path] = None,
-) -> Optional[ObjectiveScorerMetrics]:
+    file_path: Path | None = None,
+) -> ObjectiveScorerMetrics | None:
     """
     Find objective scorer metrics by evaluation hash.
 
@@ -175,7 +175,7 @@ def find_harm_metrics_by_eval_hash(
     *,
     eval_hash: str,
     harm_category: str,
-) -> Optional[HarmScorerMetrics]:
+) -> HarmScorerMetrics | None:
     """
     Find harm scorer metrics by evaluation hash.
 
@@ -195,7 +195,7 @@ def _find_metrics_by_eval_hash(
     file_path: Path,
     eval_hash: str,
     metrics_class: type[M],
-) -> Optional[M]:
+) -> M | None:
     """
     Find scorer metrics by evaluation hash in a specific file.
 
diff --git a/pyrit/score/scorer_prompt_validator.py b/pyrit/score/scorer_prompt_validator.py
index f89c93d54d..0b1140c86a 100644
--- a/pyrit/score/scorer_prompt_validator.py
+++ b/pyrit/score/scorer_prompt_validator.py
@@ -2,7 +2,7 @@
 # Licensed under the MIT license.
 
 from collections.abc import Sequence
-from typing import Optional, get_args
+from typing import get_args
 
 from pyrit.models import ChatMessageRole, Message, MessagePiece, PromptDataType
 
@@ -18,13 +18,13 @@ class ScorerPromptValidator:
     def __init__(
         self,
         *,
-        supported_data_types: Optional[Sequence[PromptDataType]] = None,
-        required_metadata: Optional[Sequence[str]] = None,
-        supported_roles: Optional[Sequence[ChatMessageRole]] = None,
-        max_pieces_in_response: Optional[int] = None,
-        max_text_length: Optional[int] = None,
-        enforce_all_pieces_valid: Optional[bool] = False,
-        raise_on_no_valid_pieces: Optional[bool] = False,
+        supported_data_types: Sequence[PromptDataType] | None = None,
+        required_metadata: Sequence[str] | None = None,
+        supported_roles: Sequence[ChatMessageRole] | None = None,
+        max_pieces_in_response: int | None = None,
+        max_text_length: int | None = None,
+        enforce_all_pieces_valid: bool | None = False,
+        raise_on_no_valid_pieces: bool | None = False,
         is_objective_required: bool = False,
     ) -> None:
         """
diff --git a/pyrit/score/true_false/audio_true_false_scorer.py b/pyrit/score/true_false/audio_true_false_scorer.py
index c10befbf44..58397a3a29 100644
--- a/pyrit/score/true_false/audio_true_false_scorer.py
+++ b/pyrit/score/true_false/audio_true_false_scorer.py
@@ -1,7 +1,6 @@
 # Copyright (c) Microsoft Corporation.
 # Licensed under the MIT license.
 
-from typing import Optional
 
 from pyrit.models import ComponentIdentifier, MessagePiece, Score
 from pyrit.score.audio_transcript_scorer import AudioTranscriptHelper
@@ -23,8 +22,8 @@ def __init__(
         self,
         *,
         text_capable_scorer: TrueFalseScorer,
-        validator: Optional[ScorerPromptValidator] = None,
-        use_entra_auth: Optional[bool] = None,
+        validator: ScorerPromptValidator | None = None,
+        use_entra_auth: bool | None = None,
     ) -> None:
         """
         Initialize the AudioTrueFalseScorer.
@@ -62,7 +61,7 @@ def _build_identifier(self) -> ComponentIdentifier:
             },
         )
 
-    async def _score_piece_async(self, message_piece: MessagePiece, *, objective: Optional[str] = None) -> list[Score]:
+    async def _score_piece_async(self, message_piece: MessagePiece, *, objective: str | None = None) -> list[Score]:
         """
         Score an audio file by transcribing it and scoring the transcript.
 
diff --git a/pyrit/score/true_false/decoding_scorer.py b/pyrit/score/true_false/decoding_scorer.py
index f9cecc5f07..a683ee9786 100644
--- a/pyrit/score/true_false/decoding_scorer.py
+++ b/pyrit/score/true_false/decoding_scorer.py
@@ -1,7 +1,6 @@
 # Copyright (c) Microsoft Corporation.
 # Licensed under the MIT license.
 
-from typing import Optional
 
 from pyrit.analytics.text_matching import ExactTextMatching, TextMatching
 from pyrit.memory.central_memory import CentralMemory
@@ -30,10 +29,10 @@ class DecodingScorer(TrueFalseScorer):
     def __init__(
         self,
         *,
-        text_matcher: Optional[TextMatching] = None,
-        categories: Optional[list[str]] = None,
+        text_matcher: TextMatching | None = None,
+        categories: list[str] | None = None,
         aggregator: TrueFalseAggregatorFunc = TrueFalseScoreAggregator.OR,
-        validator: Optional[ScorerPromptValidator] = None,
+        validator: ScorerPromptValidator | None = None,
     ) -> None:
         """
         Initialize the DecodingScorer.
@@ -65,7 +64,7 @@ def _build_identifier(self) -> ComponentIdentifier:
             },
         )
 
-    async def _score_piece_async(self, message_piece: MessagePiece, *, objective: Optional[str] = None) -> list[Score]:
+    async def _score_piece_async(self, message_piece: MessagePiece, *, objective: str | None = None) -> list[Score]:
         """
         Score the given request piece based on text matching strategy.
 
diff --git a/pyrit/score/true_false/float_scale_threshold_scorer.py b/pyrit/score/true_false/float_scale_threshold_scorer.py
index b89d5439fd..cbb565e9f8 100644
--- a/pyrit/score/true_false/float_scale_threshold_scorer.py
+++ b/pyrit/score/true_false/float_scale_threshold_scorer.py
@@ -88,8 +88,8 @@ async def _score_async(
         self,
         message: Message,
         *,
-        objective: Optional[str] = None,
-        role_filter: Optional[ChatMessageRole] = None,
+        objective: str | None = None,
+        role_filter: ChatMessageRole | None = None,
     ) -> list[Score]:
         """
         Scores the piece using the underlying float-scale scorer and thresholds the resulting score.
@@ -173,7 +173,7 @@ async def _score_async(
 
         return [score]
 
-    async def _score_piece_async(self, message_piece: MessagePiece, *, objective: Optional[str] = None) -> list[Score]:
+    async def _score_piece_async(self, message_piece: MessagePiece, *, objective: str | None = None) -> list[Score]:
         """
         Float Scale scorers do not support piecewise scoring.
 
diff --git a/pyrit/score/true_false/gandalf_scorer.py b/pyrit/score/true_false/gandalf_scorer.py
index c37469ff62..bfa0664c51 100644
--- a/pyrit/score/true_false/gandalf_scorer.py
+++ b/pyrit/score/true_false/gandalf_scorer.py
@@ -3,7 +3,6 @@
 
 import uuid
 from textwrap import dedent
-from typing import Optional
 
 import httpx
 from openai import BadRequestError
@@ -37,7 +36,7 @@ def __init__(
         *,
         level: GandalfLevel,
         chat_target: PromptTarget,
-        validator: Optional[ScorerPromptValidator] = None,
+        validator: ScorerPromptValidator | None = None,
         score_aggregator: TrueFalseAggregatorFunc = TrueFalseScoreAggregator.OR,
     ) -> None:
         """
@@ -143,7 +142,7 @@ async def _check_for_password_in_conversation_async(self, conversation_id: str)
             return ""
         return response_text
 
-    async def _score_piece_async(self, message_piece: MessagePiece, *, objective: Optional[str] = None) -> list[Score]:
+    async def _score_piece_async(self, message_piece: MessagePiece, *, objective: str | None = None) -> list[Score]:
         """
         Scores the text based on the password found in the text.
 
diff --git a/pyrit/score/true_false/markdown_injection.py b/pyrit/score/true_false/markdown_injection.py
index 517124120c..d7c0f63d5c 100644
--- a/pyrit/score/true_false/markdown_injection.py
+++ b/pyrit/score/true_false/markdown_injection.py
@@ -2,7 +2,6 @@
 # Licensed under the MIT license.
 
 import re
-from typing import Optional
 
 from pyrit.models import ComponentIdentifier, MessagePiece, Score
 from pyrit.score.scorer_prompt_validator import ScorerPromptValidator
@@ -27,7 +26,7 @@ class MarkdownInjectionScorer(TrueFalseScorer):
     def __init__(
         self,
         *,
-        validator: Optional[ScorerPromptValidator] = None,
+        validator: ScorerPromptValidator | None = None,
         score_aggregator: TrueFalseAggregatorFunc = TrueFalseScoreAggregator.OR,
     ) -> None:
         """
@@ -55,7 +54,7 @@ def _build_identifier(self) -> ComponentIdentifier:
             },
         )
 
-    async def _score_piece_async(self, message_piece: MessagePiece, *, objective: Optional[str] = None) -> list[Score]:
+    async def _score_piece_async(self, message_piece: MessagePiece, *, objective: str | None = None) -> list[Score]:
         """
         Check for markdown injection in the text. It returns True if markdown injection is detected, else False.
 
diff --git a/pyrit/score/true_false/prompt_shield_scorer.py b/pyrit/score/true_false/prompt_shield_scorer.py
index 8f048300cc..9ecab929d4 100644
--- a/pyrit/score/true_false/prompt_shield_scorer.py
+++ b/pyrit/score/true_false/prompt_shield_scorer.py
@@ -4,7 +4,7 @@
 import json
 import logging
 import uuid
-from typing import Any, Optional
+from typing import Any
 
 from pyrit.models import ComponentIdentifier, Message, MessagePiece, Score, ScoreType
 from pyrit.prompt_target import PromptShieldTarget
@@ -32,7 +32,7 @@ def __init__(
         self,
         *,
         prompt_shield_target: PromptShieldTarget,
-        validator: Optional[ScorerPromptValidator] = None,
+        validator: ScorerPromptValidator | None = None,
         score_aggregator: TrueFalseAggregatorFunc = TrueFalseScoreAggregator.OR,
     ) -> None:
         """
@@ -64,7 +64,7 @@ def _build_identifier(self) -> ComponentIdentifier:
             },
         )
 
-    async def _score_piece_async(self, message_piece: MessagePiece, *, objective: Optional[str] = None) -> list[Score]:
+    async def _score_piece_async(self, message_piece: MessagePiece, *, objective: str | None = None) -> list[Score]:
         conversation_id = str(uuid.uuid4())
 
         body = message_piece.original_value
diff --git a/pyrit/score/true_false/question_answer_scorer.py b/pyrit/score/true_false/question_answer_scorer.py
index a2346fc650..57756635dd 100644
--- a/pyrit/score/true_false/question_answer_scorer.py
+++ b/pyrit/score/true_false/question_answer_scorer.py
@@ -3,7 +3,7 @@
 
 from __future__ import annotations
 
-from typing import TYPE_CHECKING, Optional
+from typing import TYPE_CHECKING
 
 from pyrit.models import MessagePiece, Score
 from pyrit.score.scorer_prompt_validator import ScorerPromptValidator
@@ -32,8 +32,8 @@ def __init__(
         self,
         *,
         correct_answer_matching_patterns: list[str] = CORRECT_ANSWER_MATCHING_PATTERNS,
-        category: Optional[list[str]] = None,
-        validator: Optional[ScorerPromptValidator] = None,
+        category: list[str] | None = None,
+        validator: ScorerPromptValidator | None = None,
         score_aggregator: TrueFalseAggregatorFunc = TrueFalseScoreAggregator.OR,
     ) -> None:
         """
@@ -67,7 +67,7 @@ def _build_identifier(self) -> ComponentIdentifier:
             },
         )
 
-    async def _score_piece_async(self, message_piece: MessagePiece, *, objective: Optional[str] = None) -> list[Score]:
+    async def _score_piece_async(self, message_piece: MessagePiece, *, objective: str | None = None) -> list[Score]:
         """
         Score the message piece using question answering evaluation.
 
diff --git a/pyrit/score/true_false/self_ask_category_scorer.py b/pyrit/score/true_false/self_ask_category_scorer.py
index 26f28bcddf..472268d9a3 100644
--- a/pyrit/score/true_false/self_ask_category_scorer.py
+++ b/pyrit/score/true_false/self_ask_category_scorer.py
@@ -3,7 +3,6 @@
 
 import enum
 from pathlib import Path
-from typing import Optional, Union
 
 import yaml
 
@@ -42,9 +41,9 @@ def __init__(
         self,
         *,
         chat_target: PromptTarget,
-        content_classifier_path: Union[str, Path],
+        content_classifier_path: str | Path,
         score_aggregator: TrueFalseAggregatorFunc = TrueFalseScoreAggregator.OR,
-        validator: Optional[ScorerPromptValidator] = None,
+        validator: ScorerPromptValidator | None = None,
     ) -> None:
         """
         Initialize a new instance of the SelfAskCategoryScorer class.
@@ -129,7 +128,7 @@ def _content_classifier_to_string(self, categories: list[dict[str, str]]) -> str
 
         return category_descriptions
 
-    async def _score_piece_async(self, message_piece: MessagePiece, *, objective: Optional[str] = None) -> list[Score]:
+    async def _score_piece_async(self, message_piece: MessagePiece, *, objective: str | None = None) -> list[Score]:
         """
         Scores the given message using the chat target.
 
diff --git a/pyrit/score/true_false/self_ask_general_true_false_scorer.py b/pyrit/score/true_false/self_ask_general_true_false_scorer.py
index 4fc934aa42..c3d1a37002 100644
--- a/pyrit/score/true_false/self_ask_general_true_false_scorer.py
+++ b/pyrit/score/true_false/self_ask_general_true_false_scorer.py
@@ -3,7 +3,7 @@
 
 from __future__ import annotations
 
-from typing import TYPE_CHECKING, Optional
+from typing import TYPE_CHECKING
 
 from pyrit.prompt_target import CHAT_TARGET_REQUIREMENTS
 from pyrit.score.scorer_prompt_validator import ScorerPromptValidator
@@ -35,9 +35,9 @@ def __init__(
         *,
         chat_target: PromptTarget,
         system_prompt_format_string: str,
-        prompt_format_string: Optional[str] = None,
-        category: Optional[str] = None,
-        validator: Optional[ScorerPromptValidator] = None,
+        prompt_format_string: str | None = None,
+        category: str | None = None,
+        validator: ScorerPromptValidator | None = None,
         score_aggregator: TrueFalseAggregatorFunc = TrueFalseScoreAggregator.OR,
         score_value_output_key: str = "score_value",
         rationale_output_key: str = "rationale",
@@ -112,7 +112,7 @@ def _build_identifier(self) -> ComponentIdentifier:
             },
         )
 
-    async def _score_piece_async(self, message_piece: MessagePiece, *, objective: Optional[str] = None) -> list[Score]:
+    async def _score_piece_async(self, message_piece: MessagePiece, *, objective: str | None = None) -> list[Score]:
         """
         Score a single message piece using the configured prompts.
 
diff --git a/pyrit/score/true_false/self_ask_question_answer_scorer.py b/pyrit/score/true_false/self_ask_question_answer_scorer.py
index 7ea9c9a834..d4a7b78a66 100644
--- a/pyrit/score/true_false/self_ask_question_answer_scorer.py
+++ b/pyrit/score/true_false/self_ask_question_answer_scorer.py
@@ -3,7 +3,7 @@
 
 from __future__ import annotations
 
-from typing import TYPE_CHECKING, Optional
+from typing import TYPE_CHECKING
 
 from pyrit.common.path import SCORER_SEED_PROMPT_PATH
 from pyrit.common.utils import verify_and_resolve_path
@@ -38,8 +38,8 @@ def __init__(
         self,
         *,
         chat_target: PromptTarget,
-        true_false_question_path: Optional[pathlib.Path] = None,
-        validator: Optional[ScorerPromptValidator] = None,
+        true_false_question_path: pathlib.Path | None = None,
+        validator: ScorerPromptValidator | None = None,
         score_aggregator: TrueFalseAggregatorFunc = TrueFalseScoreAggregator.OR,
     ) -> None:
         """
@@ -67,7 +67,7 @@ def __init__(
             score_aggregator=score_aggregator,
         )
 
-    async def _score_piece_async(self, message_piece: MessagePiece, *, objective: Optional[str] = None) -> list[Score]:
+    async def _score_piece_async(self, message_piece: MessagePiece, *, objective: str | None = None) -> list[Score]:
         """
         Score the message piece using question answering evaluation.
 
diff --git a/pyrit/score/true_false/self_ask_refusal_scorer.py b/pyrit/score/true_false/self_ask_refusal_scorer.py
index b27fce74f2..726886ac18 100644
--- a/pyrit/score/true_false/self_ask_refusal_scorer.py
+++ b/pyrit/score/true_false/self_ask_refusal_scorer.py
@@ -3,7 +3,6 @@
 
 import enum
 from pathlib import Path
-from typing import Optional, Union
 
 from pyrit.common.path import SCORER_SEED_PROMPT_PATH
 from pyrit.models import ComponentIdentifier, MessagePiece, Score, SeedPrompt, UnvalidatedScore
@@ -69,9 +68,9 @@ def __init__(
         self,
         *,
         chat_target: PromptTarget,
-        refusal_system_prompt_path: Union[RefusalScorerPaths, Path, str] = RefusalScorerPaths.OBJECTIVE_STRICT,
-        prompt_format_string: Optional[str] = None,
-        validator: Optional[ScorerPromptValidator] = None,
+        refusal_system_prompt_path: RefusalScorerPaths | Path | str = RefusalScorerPaths.OBJECTIVE_STRICT,
+        prompt_format_string: str | None = None,
+        validator: ScorerPromptValidator | None = None,
         score_aggregator: TrueFalseAggregatorFunc = TrueFalseScoreAggregator.OR,
     ) -> None:
         """
@@ -138,7 +137,7 @@ def _build_identifier(self) -> ComponentIdentifier:
             },
         )
 
-    async def _score_piece_async(self, message_piece: MessagePiece, *, objective: Optional[str] = None) -> list[Score]:
+    async def _score_piece_async(self, message_piece: MessagePiece, *, objective: str | None = None) -> list[Score]:
         """
         Scores the prompt and determines whether the response is a refusal.
 
diff --git a/pyrit/score/true_false/self_ask_true_false_scorer.py b/pyrit/score/true_false/self_ask_true_false_scorer.py
index 7c5f860c74..8ac3121d34 100644
--- a/pyrit/score/true_false/self_ask_true_false_scorer.py
+++ b/pyrit/score/true_false/self_ask_true_false_scorer.py
@@ -4,7 +4,7 @@
 import enum
 from collections.abc import Iterator
 from pathlib import Path
-from typing import Any, Optional, Union
+from typing import Any
 
 import yaml
 
@@ -105,10 +105,10 @@ def __init__(
         self,
         *,
         chat_target: PromptTarget,
-        true_false_question_path: Optional[Union[str, Path]] = None,
-        true_false_question: Optional[TrueFalseQuestion] = None,
-        true_false_system_prompt_path: Optional[Union[str, Path]] = None,
-        validator: Optional[ScorerPromptValidator] = None,
+        true_false_question_path: str | Path | None = None,
+        true_false_question: TrueFalseQuestion | None = None,
+        true_false_system_prompt_path: str | Path | None = None,
+        validator: ScorerPromptValidator | None = None,
         score_aggregator: TrueFalseAggregatorFunc = TrueFalseScoreAggregator.OR,
     ) -> None:
         """
@@ -190,7 +190,7 @@ def _build_identifier(self) -> ComponentIdentifier:
             },
         )
 
-    async def _score_piece_async(self, message_piece: MessagePiece, *, objective: Optional[str] = None) -> list[Score]:
+    async def _score_piece_async(self, message_piece: MessagePiece, *, objective: str | None = None) -> list[Score]:
         """
         Scores the given message piece using "self-ask" for the chat target.
 
diff --git a/pyrit/score/true_false/substring_scorer.py b/pyrit/score/true_false/substring_scorer.py
index 194f5d19eb..5bcd20937a 100644
--- a/pyrit/score/true_false/substring_scorer.py
+++ b/pyrit/score/true_false/substring_scorer.py
@@ -1,7 +1,6 @@
 # Copyright (c) Microsoft Corporation.
 # Licensed under the MIT license.
 
-from typing import Optional
 
 from pyrit.analytics.text_matching import ExactTextMatching, TextMatching
 from pyrit.models import ComponentIdentifier, MessagePiece, Score
@@ -27,10 +26,10 @@ def __init__(
         self,
         *,
         substring: str,
-        text_matcher: Optional[TextMatching] = None,
-        categories: Optional[list[str]] = None,
+        text_matcher: TextMatching | None = None,
+        categories: list[str] | None = None,
         aggregator: TrueFalseAggregatorFunc = TrueFalseScoreAggregator.OR,
-        validator: Optional[ScorerPromptValidator] = None,
+        validator: ScorerPromptValidator | None = None,
     ) -> None:
         """
         Initialize the SubStringScorer.
@@ -65,7 +64,7 @@ def _build_identifier(self) -> ComponentIdentifier:
             },
         )
 
-    async def _score_piece_async(self, message_piece: MessagePiece, *, objective: Optional[str] = None) -> list[Score]:
+    async def _score_piece_async(self, message_piece: MessagePiece, *, objective: str | None = None) -> list[Score]:
         """
         Score the given message piece based on presence of the substring.
 
diff --git a/pyrit/score/true_false/true_false_composite_scorer.py b/pyrit/score/true_false/true_false_composite_scorer.py
index 148e80322c..2ac1219fee 100644
--- a/pyrit/score/true_false/true_false_composite_scorer.py
+++ b/pyrit/score/true_false/true_false_composite_scorer.py
@@ -83,8 +83,8 @@ async def _score_async(
         self,
         message: Message,
         *,
-        objective: Optional[str] = None,
-        role_filter: Optional[ChatMessageRole] = None,
+        objective: str | None = None,
+        role_filter: ChatMessageRole | None = None,
     ) -> list[Score]:
         """
         Score a request/response by combining results from all constituent scorers.
@@ -140,7 +140,7 @@ async def _score_async(
 
         return [return_score]
 
-    async def _score_piece_async(self, message_piece: MessagePiece, *, objective: Optional[str] = None) -> list[Score]:
+    async def _score_piece_async(self, message_piece: MessagePiece, *, objective: str | None = None) -> list[Score]:
         """
         Composite scorers do not support piecewise scoring.
 
diff --git a/pyrit/score/true_false/true_false_inverter_scorer.py b/pyrit/score/true_false/true_false_inverter_scorer.py
index a62d2ac287..4fff7614b3 100644
--- a/pyrit/score/true_false/true_false_inverter_scorer.py
+++ b/pyrit/score/true_false/true_false_inverter_scorer.py
@@ -15,7 +15,7 @@
 class TrueFalseInverterScorer(TrueFalseScorer):
     """A scorer that inverts a true false score."""
 
-    def __init__(self, *, scorer: TrueFalseScorer, validator: Optional[ScorerPromptValidator] = None) -> None:
+    def __init__(self, *, scorer: TrueFalseScorer, validator: ScorerPromptValidator | None = None) -> None:
         """
         Initialize the TrueFalseInverterScorer.
 
@@ -62,8 +62,8 @@ async def _score_async(
         self,
         message: Message,
         *,
-        objective: Optional[str] = None,
-        role_filter: Optional[ChatMessageRole] = None,
+        objective: str | None = None,
+        role_filter: ChatMessageRole | None = None,
     ) -> list[Score]:
         """
         Scores the piece using the underlying true-false scorer and returns the inverted score.
@@ -100,7 +100,7 @@ async def _score_async(
 
         return [inv_score]
 
-    async def _score_piece_async(self, message_piece: MessagePiece, *, objective: Optional[str] = None) -> list[Score]:
+    async def _score_piece_async(self, message_piece: MessagePiece, *, objective: str | None = None) -> list[Score]:
         """
         Indicate that True False Inverter scorers do not support piecewise scoring.
 
diff --git a/pyrit/score/true_false/true_false_scorer.py b/pyrit/score/true_false/true_false_scorer.py
index 68183f544c..8a1cf59d30 100644
--- a/pyrit/score/true_false/true_false_scorer.py
+++ b/pyrit/score/true_false/true_false_scorer.py
@@ -117,7 +117,7 @@ def get_scorer_metrics(self) -> Optional["ObjectiveScorerMetrics"]:
 
         return find_objective_metrics_by_eval_hash(eval_hash=eval_hash, file_path=result_file)
 
-    async def _score_async(self, message: Message, *, objective: Optional[str] = None) -> list[Score]:
+    async def _score_async(self, message: Message, *, objective: str | None = None) -> list[Score]:
         """
         Score the given request response asynchronously.
 
@@ -158,7 +158,7 @@ async def _score_async(self, message: Message, *, objective: Optional[str] = Non
             )
         ]
 
-    def _build_fallback_score(self, *, message: Message, objective: Optional[str]) -> list[Score]:
+    def _build_fallback_score(self, *, message: Message, objective: str | None) -> list[Score]:
         """
         Build a single-element list containing a ``false`` score when no pieces could be scored.
 
diff --git a/pyrit/score/true_false/video_true_false_scorer.py b/pyrit/score/true_false/video_true_false_scorer.py
index d1895aa4bb..5c45eae477 100644
--- a/pyrit/score/true_false/video_true_false_scorer.py
+++ b/pyrit/score/true_false/video_true_false_scorer.py
@@ -1,7 +1,6 @@
 # Copyright (c) Microsoft Corporation.
 # Licensed under the MIT license.
 
-from typing import Optional
 
 from pyrit.models import ComponentIdentifier, MessagePiece, Score
 from pyrit.score.scorer_prompt_validator import ScorerPromptValidator
@@ -30,11 +29,11 @@ def __init__(
         self,
         *,
         image_capable_scorer: TrueFalseScorer,
-        audio_scorer: Optional[TrueFalseScorer] = None,
-        num_sampled_frames: Optional[int] = None,
-        validator: Optional[ScorerPromptValidator] = None,
-        image_objective_template: Optional[str] = VideoHelper._DEFAULT_IMAGE_OBJECTIVE_TEMPLATE,
-        audio_objective_template: Optional[str] = None,
+        audio_scorer: TrueFalseScorer | None = None,
+        num_sampled_frames: int | None = None,
+        validator: ScorerPromptValidator | None = None,
+        image_objective_template: str | None = VideoHelper._DEFAULT_IMAGE_OBJECTIVE_TEMPLATE,
+        audio_objective_template: str | None = None,
     ) -> None:
         """
         Initialize the VideoTrueFalseScorer.
@@ -94,7 +93,7 @@ def _build_identifier(self) -> ComponentIdentifier:
             },
         )
 
-    async def _score_piece_async(self, message_piece: MessagePiece, *, objective: Optional[str] = None) -> list[Score]:
+    async def _score_piece_async(self, message_piece: MessagePiece, *, objective: str | None = None) -> list[Score]:
         """
         Score a single video piece by extracting frames and optionally audio, then aggregating their scores.
 
diff --git a/pyrit/score/video_scorer.py b/pyrit/score/video_scorer.py
index 400d2522a9..b4fbecad38 100644
--- a/pyrit/score/video_scorer.py
+++ b/pyrit/score/video_scorer.py
@@ -6,7 +6,6 @@
 import tempfile
 import uuid
 from pathlib import Path
-from typing import Optional
 
 from pyrit.memory import CentralMemory
 from pyrit.models import MessagePiece, Score
@@ -43,9 +42,9 @@ def __init__(
         self,
         *,
         image_capable_scorer: Scorer,
-        num_sampled_frames: Optional[int] = None,
-        image_objective_template: Optional[str] = _DEFAULT_IMAGE_OBJECTIVE_TEMPLATE,
-        audio_objective_template: Optional[str] = None,
+        num_sampled_frames: int | None = None,
+        image_objective_template: str | None = _DEFAULT_IMAGE_OBJECTIVE_TEMPLATE,
+        audio_objective_template: str | None = None,
     ) -> None:
         """
         Initialize the base video scorer.
@@ -95,7 +94,7 @@ def _validate_audio_scorer(scorer: Scorer) -> None:
                 f"Supported types: {scorer._validator._supported_data_types}"
             )
 
-    async def _score_frames_async(self, *, message_piece: MessagePiece, objective: Optional[str] = None) -> list[Score]:
+    async def _score_frames_async(self, *, message_piece: MessagePiece, objective: str | None = None) -> list[Score]:
         """
         Extract frames from video and score them.
 
@@ -211,7 +210,7 @@ def _extract_frames(self, video_path: str) -> list[str]:
         return frame_paths
 
     async def _score_video_audio_async(
-        self, *, message_piece: MessagePiece, audio_scorer: Optional[Scorer] = None, objective: Optional[str] = None
+        self, *, message_piece: MessagePiece, audio_scorer: Scorer | None = None, objective: str | None = None
     ) -> list[Score]:
         """
         Extract and score audio from the video.
diff --git a/pyrit/setup/configuration_loader.py b/pyrit/setup/configuration_loader.py
index 0af45c4adf..51c1c30e9a 100644
--- a/pyrit/setup/configuration_loader.py
+++ b/pyrit/setup/configuration_loader.py
@@ -11,7 +11,7 @@
 import pathlib
 from collections.abc import Sequence
 from dataclasses import dataclass, field
-from typing import TYPE_CHECKING, Any, Optional, Union
+from typing import TYPE_CHECKING, Any
 
 from pyrit.common.path import DEFAULT_CONFIG_PATH
 from pyrit.common.yaml_loadable import YamlLoadable
@@ -29,8 +29,8 @@
 
 # Type alias for YAML-serializable values that can be passed as initializer args
 # This matches what YAML can represent: primitives, lists, and nested dicts
-YamlPrimitive = Union[str, int, float, bool, None]
-YamlValue = Union[YamlPrimitive, list["YamlValue"], dict[str, "YamlValue"]]
+YamlPrimitive = str | int | float | bool | None
+YamlValue = YamlPrimitive | list["YamlValue"] | dict[str, "YamlValue"]
 
 # Mapping from snake_case config values to internal constants
 _MEMORY_DB_TYPE_MAP: dict[str, str] = {
@@ -51,7 +51,7 @@ class InitializerConfig:
     """
 
     name: str
-    args: Optional[dict[str, YamlValue]] = None
+    args: dict[str, YamlValue] | None = None
 
 
 @dataclass
@@ -77,7 +77,7 @@ class ScenarioConfig:
     """
 
     name: str
-    args: Optional[dict[str, YamlValue]] = None
+    args: dict[str, YamlValue] | None = None
 
 
 def _scenario_config_to_dict(config: ScenarioConfig) -> dict[str, Any]:
@@ -137,16 +137,16 @@ class ConfigurationLoader(YamlLoadable):
     """
 
     memory_db_type: str = "sqlite"
-    initializers: list[Union[str, dict[str, Any]]] = field(default_factory=list)
-    initialization_scripts: Optional[list[str]] = None
-    env_files: Optional[list[str]] = None
+    initializers: list[str | dict[str, Any]] = field(default_factory=list)
+    initialization_scripts: list[str] | None = None
+    env_files: list[str] | None = None
     silent: bool = False
-    operator: Optional[str] = None
-    operation: Optional[str] = None
-    scenario: Optional[Union[str, dict[str, Any]]] = None
+    operator: str | None = None
+    operation: str | None = None
+    scenario: str | dict[str, Any] | None = None
     max_concurrent_scenario_runs: int = 3
     allow_custom_initializers: bool = False
-    server: Optional[dict[str, Any]] = None
+    server: dict[str, Any] | None = None
     extensions: dict[str, Any] = field(default_factory=dict)
 
     def __post_init__(self) -> None:
@@ -229,7 +229,7 @@ def _normalize_scenario(self) -> None:
             ValueError: For any other shape.
         """
         if self.scenario is None:
-            self._scenario_config: Optional[ScenarioConfig] = None
+            self._scenario_config: ScenarioConfig | None = None
             return
 
         if isinstance(self.scenario, str):
@@ -263,7 +263,7 @@ def _normalize_server(self) -> None:
             ValueError: If ``server`` is not ``None`` or a dict, or if ``url`` is not a string.
         """
         if self.server is None:
-            self._server_config: Optional[ServerConfig] = None
+            self._server_config: ServerConfig | None = None
             return
 
         if isinstance(self.server, dict):
@@ -276,12 +276,12 @@ def _normalize_server(self) -> None:
         raise ValueError(f"Server entry must be a dict, got: {type(self.server).__name__}")
 
     @property
-    def server_config(self) -> Optional[ServerConfig]:
+    def server_config(self) -> ServerConfig | None:
         """The normalized ``server:`` block, or ``None`` when not configured."""
         return self._server_config
 
     @property
-    def scenario_config(self) -> Optional[ScenarioConfig]:
+    def scenario_config(self) -> ScenarioConfig | None:
         """The normalized ``scenario:`` block, or ``None`` when not configured."""
         return self._scenario_config
 
@@ -313,12 +313,12 @@ def from_dict(cls, data: dict[str, Any]) -> "ConfigurationLoader":
 
     @staticmethod
     def load_with_overrides(
-        config_file: Optional[pathlib.Path] = None,
+        config_file: pathlib.Path | None = None,
         *,
-        memory_db_type: Optional[str] = None,
-        initializers: Optional[Sequence[Union[str, dict[str, Any]]]] = None,
-        initialization_scripts: Optional[Sequence[str]] = None,
-        env_files: Optional[Sequence[str]] = None,
+        memory_db_type: str | None = None,
+        initializers: Sequence[str | dict[str, Any]] | None = None,
+        initialization_scripts: Sequence[str] | None = None,
+        env_files: Sequence[str] | None = None,
     ) -> "ConfigurationLoader":
         """
         Load configuration with optional overrides.
@@ -487,7 +487,7 @@ def resolve_initializers(self) -> Sequence["PyRITInitializer"]:
 
         return resolved
 
-    def resolve_initialization_scripts(self) -> Optional[Sequence[pathlib.Path]]:
+    def resolve_initialization_scripts(self) -> Sequence[pathlib.Path] | None:
         """
         Resolve initialization script paths.
 
@@ -512,7 +512,7 @@ def resolve_initialization_scripts(self) -> Optional[Sequence[pathlib.Path]]:
 
         return resolved
 
-    def resolve_env_files(self) -> Optional[Sequence[pathlib.Path]]:
+    def resolve_env_files(self) -> Sequence[pathlib.Path] | None:
         """
         Resolve environment file paths.
 
@@ -564,7 +564,7 @@ async def initialize_pyrit_async(self) -> None:
 
 
 async def initialize_from_config_async(
-    config_path: Optional[Union[str, pathlib.Path]] = None,
+    config_path: str | pathlib.Path | None = None,
 ) -> ConfigurationLoader:
     """
     Initialize PyRIT from a configuration file.
diff --git a/pyrit/setup/initialization.py b/pyrit/setup/initialization.py
index 5d3dfe6663..ab8caa95ed 100644
--- a/pyrit/setup/initialization.py
+++ b/pyrit/setup/initialization.py
@@ -3,7 +3,7 @@
 import logging
 import pathlib
 from collections.abc import Sequence
-from typing import TYPE_CHECKING, Any, Literal, Optional, Union, get_args
+from typing import TYPE_CHECKING, Any, Literal, get_args
 
 import dotenv
 
@@ -27,7 +27,7 @@
 MemoryDatabaseType = Literal["InMemory", "SQLite", "AzureSQL"]
 
 
-def _load_environment_files(env_files: Optional[Sequence[pathlib.Path]], *, silent: bool = False) -> None:
+def _load_environment_files(env_files: Sequence[pathlib.Path] | None, *, silent: bool = False) -> None:
     """
     Load environment files in the order they are provided.
     Later files override values from earlier files.
@@ -95,9 +95,7 @@ def _print_msg(message: str, quiet: bool, log: bool) -> None:
         logger.info(message)
 
 
-def _load_initializers_from_scripts(
-    *, script_paths: Sequence[Union[str, pathlib.Path]]
-) -> Sequence["PyRITInitializer"]:
+def _load_initializers_from_scripts(*, script_paths: Sequence[str | pathlib.Path]) -> Sequence["PyRITInitializer"]:
     """
     Load PyRITInitializer instances from external Python files.
 
@@ -228,11 +226,11 @@ async def _execute_initializers_async(*, initializers: Sequence["PyRITInitialize
 
 
 async def initialize_pyrit_async(
-    memory_db_type: Union[MemoryDatabaseType, str],
+    memory_db_type: MemoryDatabaseType | str,
     *,
-    initialization_scripts: Optional[Sequence[Union[str, pathlib.Path]]] = None,
-    initializers: Optional[Sequence["PyRITInitializer"]] = None,
-    env_files: Optional[Sequence[pathlib.Path]] = None,
+    initialization_scripts: Sequence[str | pathlib.Path] | None = None,
+    initializers: Sequence["PyRITInitializer"] | None = None,
+    env_files: Sequence[pathlib.Path] | None = None,
     silent: bool = False,
     **memory_instance_kwargs: Any,
 ) -> None:
diff --git a/pyrit/setup/initializers/components/targets.py b/pyrit/setup/initializers/components/targets.py
index fd0284c7d9..017bb873bf 100644
--- a/pyrit/setup/initializers/components/targets.py
+++ b/pyrit/setup/initializers/components/targets.py
@@ -17,7 +17,7 @@
 from collections import defaultdict
 from dataclasses import dataclass, field
 from enum import Enum
-from typing import Any, Optional
+from typing import Any
 
 from pyrit.auth import get_azure_openai_auth, get_azure_token_provider
 from pyrit.common.parameter import Parameter
@@ -71,9 +71,9 @@ class TargetConfig:
     target_class: type[PromptTarget]
     endpoint_var: str
     key_var: str = ""  # Empty string means no auth required
-    model_var: Optional[str] = None
-    underlying_model_var: Optional[str] = None
-    temperature: Optional[float] = None
+    model_var: str | None = None
+    underlying_model_var: str | None = None
+    temperature: float | None = None
     extra_kwargs: dict[str, Any] = field(default_factory=dict)
     tags: list[TargetInitializerTags] = field(default_factory=lambda: [TargetInitializerTags.DEFAULT])
     default_objective_target: bool = False
diff --git a/tests/integration/mocks.py b/tests/integration/mocks.py
index 512a4b5986..f222f501e6 100644
--- a/tests/integration/mocks.py
+++ b/tests/integration/mocks.py
@@ -2,7 +2,6 @@
 # Licensed under the MIT license.
 
 from collections.abc import Generator
-from typing import Optional
 
 from sqlalchemy import inspect
 
@@ -57,8 +56,8 @@ def set_system_prompt(
         *,
         system_prompt: str,
         conversation_id: str,
-        attack_identifier: Optional[ComponentIdentifier] = None,
-        labels: Optional[dict[str, str]] = None,
+        attack_identifier: ComponentIdentifier | None = None,
+        labels: dict[str, str] | None = None,
     ) -> None:
         self.system_prompt = system_prompt
         if self._memory:
diff --git a/tests/unit/analytics/test_result_analysis.py b/tests/unit/analytics/test_result_analysis.py
index 21d18541ed..8edf1e8ef7 100644
--- a/tests/unit/analytics/test_result_analysis.py
+++ b/tests/unit/analytics/test_result_analysis.py
@@ -2,7 +2,6 @@
 # Licensed under the MIT license.
 
 from datetime import datetime, timedelta, timezone
-from typing import Optional
 from unittest.mock import MagicMock
 
 import pytest
@@ -27,13 +26,13 @@
 # helpers
 def make_attack(
     outcome: AttackOutcome,
-    attack_type: Optional[str] = "default",
+    attack_type: str | None = "default",
     conversation_id: str = "conv-1",
 ) -> AttackResult:
     """
     Minimal valid AttackResult for analytics tests.
     """
-    attack_identifier: Optional[ComponentIdentifier] = None
+    attack_identifier: ComponentIdentifier | None = None
     if attack_type is not None:
         attack_identifier = ComponentIdentifier(class_name=attack_type, class_module="tests.unit.analytics")
 
@@ -190,7 +189,7 @@ def _make_attack_with_target(
     target: ComponentIdentifier,
     *,
     outcome: AttackOutcome = AttackOutcome.SUCCESS,
-    timestamp: Optional[datetime] = None,
+    timestamp: datetime | None = None,
 ) -> AttackResult:
     technique = ComponentIdentifier(
         class_name="PromptSendingAttack",
diff --git a/tests/unit/common/test_pyrit_default_value.py b/tests/unit/common/test_pyrit_default_value.py
index e29981a6f3..cbd9584293 100644
--- a/tests/unit/common/test_pyrit_default_value.py
+++ b/tests/unit/common/test_pyrit_default_value.py
@@ -1,7 +1,6 @@
 # Copyright (c) Microsoft Corporation.
 # Licensed under the MIT license.
 
-from typing import Optional
 
 import pytest
 
@@ -28,7 +27,7 @@ def test_no_defaults_configured_returns_none(self) -> None:
 
         class TestClass:
             @apply_defaults
-            def __init__(self, *, param1: Optional[str] = None, param2: Optional[int] = None) -> None:
+            def __init__(self, *, param1: str | None = None, param2: int | None = None) -> None:
                 self.param1 = param1
                 self.param2 = param2
 
@@ -41,7 +40,7 @@ def test_single_default_value_applied(self) -> None:
 
         class TestClass:
             @apply_defaults
-            def __init__(self, *, param1: Optional[str] = None) -> None:
+            def __init__(self, *, param1: str | None = None) -> None:
                 self.param1 = param1
 
         set_default_value(class_type=TestClass, parameter_name="param1", value="default_value")
@@ -55,7 +54,7 @@ def test_multiple_default_values_applied(self) -> None:
         class TestClass:
             @apply_defaults
             def __init__(
-                self, *, param1: Optional[str] = None, param2: Optional[int] = None, param3: Optional[float] = None
+                self, *, param1: str | None = None, param2: int | None = None, param3: float | None = None
             ) -> None:
                 self.param1 = param1
                 self.param2 = param2
@@ -75,7 +74,7 @@ def test_explicit_value_overrides_default(self) -> None:
 
         class TestClass:
             @apply_defaults
-            def __init__(self, *, param1: Optional[str] = None, param2: Optional[int] = None) -> None:
+            def __init__(self, *, param1: str | None = None, param2: int | None = None) -> None:
                 self.param1 = param1
                 self.param2 = param2
 
@@ -92,7 +91,7 @@ def test_partial_override_uses_remaining_defaults(self) -> None:
         class TestClass:
             @apply_defaults
             def __init__(
-                self, *, param1: Optional[str] = None, param2: Optional[int] = None, param3: Optional[float] = None
+                self, *, param1: str | None = None, param2: int | None = None, param3: float | None = None
             ) -> None:
                 self.param1 = param1
                 self.param2 = param2
@@ -115,9 +114,9 @@ class TestClass:
             def __init__(
                 self,
                 *,
-                param_int: Optional[int] = None,
-                param_bool: Optional[bool] = None,
-                param_str: Optional[str] = None,
+                param_int: int | None = None,
+                param_bool: bool | None = None,
+                param_str: str | None = None,
             ) -> None:
                 self.param_int = param_int
                 self.param_bool = param_bool
@@ -145,13 +144,13 @@ def test_subclass_inherits_parent_defaults(self) -> None:
 
         class ParentClass:
             @apply_defaults
-            def __init__(self, *, param1: Optional[str] = None, param2: Optional[int] = None) -> None:
+            def __init__(self, *, param1: str | None = None, param2: int | None = None) -> None:
                 self.param1 = param1
                 self.param2 = param2
 
         class ChildClass(ParentClass):
             @apply_defaults
-            def __init__(self, *, param1: Optional[str] = None, param2: Optional[int] = None) -> None:
+            def __init__(self, *, param1: str | None = None, param2: int | None = None) -> None:
                 super().__init__(param1=param1, param2=param2)
 
         set_default_value(class_type=ParentClass, parameter_name="param1", value="parent_value")
@@ -166,13 +165,13 @@ def test_subclass_specific_defaults_override_parent(self) -> None:
 
         class ParentClass:
             @apply_defaults
-            def __init__(self, *, param1: Optional[str] = None, param2: Optional[int] = None) -> None:
+            def __init__(self, *, param1: str | None = None, param2: int | None = None) -> None:
                 self.param1 = param1
                 self.param2 = param2
 
         class ChildClass(ParentClass):
             @apply_defaults
-            def __init__(self, *, param1: Optional[str] = None, param2: Optional[int] = None) -> None:
+            def __init__(self, *, param1: str | None = None, param2: int | None = None) -> None:
                 super().__init__(param1=param1, param2=param2)
 
         set_default_value(class_type=ParentClass, parameter_name="param1", value="parent_value")
@@ -189,19 +188,19 @@ def test_multiple_inheritance_levels(self) -> None:
 
         class GrandParent:
             @apply_defaults
-            def __init__(self, *, param1: Optional[str] = None) -> None:
+            def __init__(self, *, param1: str | None = None) -> None:
                 self.param1 = param1
 
         class Parent(GrandParent):
             @apply_defaults
-            def __init__(self, *, param1: Optional[str] = None, param2: Optional[int] = None) -> None:
+            def __init__(self, *, param1: str | None = None, param2: int | None = None) -> None:
                 super().__init__(param1=param1)
                 self.param2 = param2
 
         class Child(Parent):
             @apply_defaults
             def __init__(
-                self, *, param1: Optional[str] = None, param2: Optional[int] = None, param3: Optional[float] = None
+                self, *, param1: str | None = None, param2: int | None = None, param3: float | None = None
             ) -> None:
                 super().__init__(param1=param1, param2=param2)
                 self.param3 = param3
@@ -220,12 +219,12 @@ def test_parent_not_affected_by_child_defaults(self) -> None:
 
         class ParentClass:
             @apply_defaults
-            def __init__(self, *, param1: Optional[str] = None) -> None:
+            def __init__(self, *, param1: str | None = None) -> None:
                 self.param1 = param1
 
         class ChildClass(ParentClass):
             @apply_defaults
-            def __init__(self, *, param1: Optional[str] = None) -> None:
+            def __init__(self, *, param1: str | None = None) -> None:
                 super().__init__(param1=param1)
 
         set_default_value(class_type=ChildClass, parameter_name="param1", value="child_value")
@@ -354,7 +353,7 @@ def test_set_default_value_stores_value(self) -> None:
 
         class TestClass:
             @apply_defaults
-            def __init__(self, *, param1: Optional[str] = None) -> None:
+            def __init__(self, *, param1: str | None = None) -> None:
                 self.param1 = param1
 
         set_default_value(class_type=TestClass, parameter_name="param1", value="stored_value")
@@ -367,7 +366,7 @@ def test_set_default_value_overwrites_existing(self) -> None:
 
         class TestClass:
             @apply_defaults
-            def __init__(self, *, param1: Optional[str] = None) -> None:
+            def __init__(self, *, param1: str | None = None) -> None:
                 self.param1 = param1
 
         set_default_value(class_type=TestClass, parameter_name="param1", value="first_value")
@@ -392,9 +391,9 @@ class OpenAIChatTarget:
             def __init__(
                 self,
                 *,
-                temperature: Optional[float] = None,
-                top_p: Optional[float] = None,
-                max_tokens: Optional[int] = None,
+                temperature: float | None = None,
+                top_p: float | None = None,
+                max_tokens: int | None = None,
             ) -> None:
                 self.temperature = temperature
                 self.top_p = top_p
@@ -405,9 +404,9 @@ class AzureOpenAIChatTarget(OpenAIChatTarget):
             def __init__(
                 self,
                 *,
-                temperature: Optional[float] = None,
-                top_p: Optional[float] = None,
-                max_tokens: Optional[int] = None,
+                temperature: float | None = None,
+                top_p: float | None = None,
+                max_tokens: int | None = None,
             ) -> None:
                 super().__init__(temperature=temperature, top_p=top_p, max_tokens=max_tokens)
 
@@ -441,12 +440,12 @@ def test_multiple_classes_independent_defaults(self) -> None:
 
         class ClassA:
             @apply_defaults
-            def __init__(self, *, param: Optional[str] = None) -> None:
+            def __init__(self, *, param: str | None = None) -> None:
                 self.param = param
 
         class ClassB:
             @apply_defaults
-            def __init__(self, *, param: Optional[str] = None) -> None:
+            def __init__(self, *, param: str | None = None) -> None:
                 self.param = param
 
         set_default_value(class_type=ClassA, parameter_name="param", value="value_a")
@@ -471,7 +470,7 @@ def test_reset_clears_all_defaults(self) -> None:
 
         class TestClass:
             @apply_defaults
-            def __init__(self, *, param1: Optional[str] = None, param2: Optional[int] = None) -> None:
+            def __init__(self, *, param1: str | None = None, param2: int | None = None) -> None:
                 self.param1 = param1
                 self.param2 = param2
 
@@ -497,12 +496,12 @@ def test_reset_affects_multiple_classes(self) -> None:
 
         class ClassA:
             @apply_defaults
-            def __init__(self, *, param: Optional[str] = None) -> None:
+            def __init__(self, *, param: str | None = None) -> None:
                 self.param = param
 
         class ClassB:
             @apply_defaults
-            def __init__(self, *, param: Optional[int] = None) -> None:
+            def __init__(self, *, param: int | None = None) -> None:
                 self.param = param
 
         # Set defaults for multiple classes
@@ -523,7 +522,7 @@ def test_reset_allows_setting_new_defaults(self) -> None:
 
         class TestClass:
             @apply_defaults
-            def __init__(self, *, param: Optional[str] = None) -> None:
+            def __init__(self, *, param: str | None = None) -> None:
                 self.param = param
 
         # Set initial default
@@ -544,7 +543,7 @@ def test_reset_with_no_defaults_does_nothing(self) -> None:
 
         class TestClass:
             @apply_defaults
-            def __init__(self, *, param: Optional[str] = None) -> None:
+            def __init__(self, *, param: str | None = None) -> None:
                 self.param = param
 
         # Reset when no defaults are set
@@ -562,12 +561,12 @@ def test_reset_clears_inheritance_based_defaults(self) -> None:
 
         class ParentClass:
             @apply_defaults
-            def __init__(self, *, param: Optional[str] = None) -> None:
+            def __init__(self, *, param: str | None = None) -> None:
                 self.param = param
 
         class ChildClass(ParentClass):
             @apply_defaults
-            def __init__(self, *, param: Optional[str] = None) -> None:
+            def __init__(self, *, param: str | None = None) -> None:
                 super().__init__(param=param)
 
         # Set defaults for both parent and child
@@ -588,7 +587,7 @@ def test_reset_clears_include_subclasses_flag_variations(self) -> None:
 
         class TestClass:
             @apply_defaults
-            def __init__(self, *, param1: Optional[str] = None, param2: Optional[str] = None) -> None:
+            def __init__(self, *, param1: str | None = None, param2: str | None = None) -> None:
                 self.param1 = param1
                 self.param2 = param2
 
@@ -761,7 +760,7 @@ def __init__(
                 self,
                 *,
                 required_param: str = REQUIRED_VALUE,  # type: ignore[assignment]
-                optional_param: Optional[str] = None,
+                optional_param: str | None = None,
             ) -> None:
                 self.required_param = required_param
                 self.optional_param = optional_param
@@ -847,7 +846,7 @@ def test_required_value_none_is_different(self) -> None:
 
         class TestClass1:
             @apply_defaults
-            def __init__(self, *, param: Optional[str] = None) -> None:
+            def __init__(self, *, param: str | None = None) -> None:
                 self.param = param
 
         class TestClass2:
diff --git a/tests/unit/executor/attack/component/test_conversation_manager.py b/tests/unit/executor/attack/component/test_conversation_manager.py
index ed56813139..47d8678b7d 100644
--- a/tests/unit/executor/attack/component/test_conversation_manager.py
+++ b/tests/unit/executor/attack/component/test_conversation_manager.py
@@ -18,7 +18,6 @@
 """
 
 import uuid
-from typing import Optional
 from unittest.mock import AsyncMock, MagicMock, patch
 
 import pytest
@@ -56,7 +55,7 @@ class _TestAttackContext(AttackContext):
     """Concrete AttackContext for testing."""
 
     # Add last_score to match MultiTurnAttackContext behavior for testing
-    last_score: Optional[Score] = None
+    last_score: Score | None = None
 
 
 # =============================================================================
diff --git a/tests/unit/executor/attack/compound/test_sequential_attack.py b/tests/unit/executor/attack/compound/test_sequential_attack.py
index 79865e8f55..68cf8180d3 100644
--- a/tests/unit/executor/attack/compound/test_sequential_attack.py
+++ b/tests/unit/executor/attack/compound/test_sequential_attack.py
@@ -3,7 +3,6 @@
 
 """Tests for ``SequentialAttack``."""
 
-from typing import Optional
 from unittest.mock import AsyncMock, MagicMock, patch
 
 import pytest
@@ -35,7 +34,7 @@ def _make_seed_group(objective: str = "obj") -> SeedAttackGroup:
 def _make_context(
     *,
     objective: str = "obj",
-    labels: Optional[dict[str, str]] = None,
+    labels: dict[str, str] | None = None,
 ) -> AttackContext[AttackParameters]:
     params_type = AttackParameters.excluding("next_message", "prepended_conversation")
     return AttackContext(params=params_type(objective=objective, memory_labels=labels or {}))
diff --git a/tests/unit/executor/attack/multi_turn/test_crescendo.py b/tests/unit/executor/attack/multi_turn/test_crescendo.py
index 1bd1c38f46..e8e295ba88 100644
--- a/tests/unit/executor/attack/multi_turn/test_crescendo.py
+++ b/tests/unit/executor/attack/multi_turn/test_crescendo.py
@@ -4,7 +4,6 @@
 import json
 import uuid
 from pathlib import Path
-from typing import Optional
 from unittest.mock import AsyncMock, MagicMock, patch
 
 import pytest
@@ -85,11 +84,11 @@ def create_score(
     *,
     score_type: ScoreType,
     score_value: str,
-    score_category: Optional[list[str]] = None,
+    score_category: list[str] | None = None,
     scorer_class: str,
     score_rationale: str = "Test rationale",
     score_value_description: str = "Test description",
-    score_metadata: Optional[dict] = None,
+    score_metadata: dict | None = None,
 ) -> Score:
     """Create a score with common defaults.
 
@@ -254,10 +253,10 @@ def create_attack(
         *,
         objective_target: MagicMock,
         adversarial_chat: MagicMock,
-        objective_scorer: Optional[MagicMock] = None,
-        refusal_scorer: Optional[MagicMock] = None,
-        prompt_normalizer: Optional[MagicMock] = None,
-        system_prompt_path: Optional[Path] = None,
+        objective_scorer: MagicMock | None = None,
+        refusal_scorer: MagicMock | None = None,
+        prompt_normalizer: MagicMock | None = None,
+        system_prompt_path: Path | None = None,
         **kwargs,
     ) -> CrescendoAttack:
         """Create a CrescendoAttack instance with flexible configuration.
@@ -909,7 +908,7 @@ async def test_parse_adversarial_response_with_various_inputs(
         mock_objective_target: MagicMock,
         mock_adversarial_chat: MagicMock,
         response_json: str,
-        expected_error: Optional[str],
+        expected_error: str | None,
     ):
         """Test parsing adversarial response with various inputs.
 
diff --git a/tests/unit/executor/attack/multi_turn/test_red_teaming.py b/tests/unit/executor/attack/multi_turn/test_red_teaming.py
index 173b9c2f22..e5e14f1eff 100644
--- a/tests/unit/executor/attack/multi_turn/test_red_teaming.py
+++ b/tests/unit/executor/attack/multi_turn/test_red_teaming.py
@@ -3,7 +3,6 @@
 
 import uuid
 from pathlib import Path
-from typing import Union
 from unittest.mock import AsyncMock, MagicMock, patch
 
 import pytest
@@ -215,7 +214,7 @@ def test_init_with_seed_prompt_variations(
         mock_objective_target: MagicMock,
         mock_objective_scorer: MagicMock,
         mock_adversarial_chat: MagicMock,
-        seed_prompt: Union[str, SeedPrompt],
+        seed_prompt: str | SeedPrompt,
         expected_value: str,
         expected_type: type,
     ):
diff --git a/tests/unit/executor/attack/multi_turn/test_tree_of_attacks.py b/tests/unit/executor/attack/multi_turn/test_tree_of_attacks.py
index 5c805455bf..aebd00702b 100644
--- a/tests/unit/executor/attack/multi_turn/test_tree_of_attacks.py
+++ b/tests/unit/executor/attack/multi_turn/test_tree_of_attacks.py
@@ -6,7 +6,7 @@
 import logging
 import uuid
 from dataclasses import dataclass, field
-from typing import Any, Optional, cast
+from typing import Any, cast
 from unittest.mock import AsyncMock, MagicMock, patch
 
 import pytest
@@ -50,11 +50,11 @@ class NodeMockConfig:
     """Configuration for creating mock _TreeOfAttacksNode objects."""
 
     node_id: str = field(default_factory=lambda: str(uuid.uuid4()))
-    parent_id: Optional[str] = None
+    parent_id: str | None = None
     prompt_sent: bool = False
     completed: bool = True
     off_topic: bool = False
-    objective_score_value: Optional[float] = None
+    objective_score_value: float | None = None
     auxiliary_scores: dict[str, float] = field(default_factory=dict)
     objective_target_conversation_id: str = field(default_factory=lambda: str(uuid.uuid4()))
     adversarial_chat_conversation_id: str = field(default_factory=lambda: str(uuid.uuid4()))
@@ -64,7 +64,7 @@ class MockNodeFactory:
     """Factory for creating mock _TreeOfAttacksNode objects."""
 
     @staticmethod
-    def create_node(config: Optional[NodeMockConfig] = None) -> "_TreeOfAttacksNode":
+    def create_node(config: NodeMockConfig | None = None) -> "_TreeOfAttacksNode":
         """Create a mock _TreeOfAttacksNode with the given configuration."""
         if config is None:
             config = NodeMockConfig()
@@ -150,14 +150,14 @@ class AttackBuilder:
     """Builder for creating TreeOfAttacksWithPruningAttack instances with common configurations."""
 
     def __init__(self) -> None:
-        self.objective_target: Optional[PromptTarget] = None
-        self.adversarial_chat: Optional[PromptTarget] = None
-        self.objective_scorer: Optional[Scorer] = None
+        self.objective_target: PromptTarget | None = None
+        self.adversarial_chat: PromptTarget | None = None
+        self.objective_scorer: Scorer | None = None
         self.auxiliary_scorers: list[Scorer] = []
         self.tree_params: dict[str, Any] = {}
-        self.converters: Optional[AttackConverterConfig] = None
+        self.converters: AttackConverterConfig | None = None
         self.successful_threshold: float = 0.8
-        self.prompt_normalizer: Optional[PromptNormalizer] = None
+        self.prompt_normalizer: PromptNormalizer | None = None
         self._supports_multi_turn: bool = True
 
     def with_default_mocks(self) -> "AttackBuilder":
diff --git a/tests/unit/executor/attack/test_attack_parameter_consistency.py b/tests/unit/executor/attack/test_attack_parameter_consistency.py
index a23dd6daca..963e84d3e4 100644
--- a/tests/unit/executor/attack/test_attack_parameter_consistency.py
+++ b/tests/unit/executor/attack/test_attack_parameter_consistency.py
@@ -10,7 +10,6 @@
 
 import uuid
 from contextlib import suppress
-from typing import Optional
 from unittest.mock import AsyncMock, MagicMock
 
 import pytest
@@ -911,7 +910,7 @@ def _assert_prepended_text_in_adversarial_context(
     *,
     prepended_conversation: list[Message],
     adversarial_chat_conversation_id: str,
-    adversarial_chat_mock: Optional[MagicMock] = None,
+    adversarial_chat_mock: MagicMock | None = None,
 ) -> None:
     """
     Assert that text content from prepended conversation appears in adversarial chat context.
diff --git a/tests/unit/memory/memory_interface/test_interface_attack_results.py b/tests/unit/memory/memory_interface/test_interface_attack_results.py
index cdb611e64b..61fbc860b9 100644
--- a/tests/unit/memory/memory_interface/test_interface_attack_results.py
+++ b/tests/unit/memory/memory_interface/test_interface_attack_results.py
@@ -3,7 +3,7 @@
 
 
 import uuid
-from typing import TYPE_CHECKING, Optional
+from typing import TYPE_CHECKING
 
 import pytest
 
@@ -1270,7 +1270,7 @@ def test_get_unique_attack_labels_deduplicates_across_sources(sqlite_instance: M
 def _make_attack_result_with_identifier(
     conversation_id: str,
     class_name: str,
-    converter_class_names: Optional[list[str]] = None,
+    converter_class_names: list[str] | None = None,
 ) -> AttackResult:
     """Helper to create an AttackResult with a ComponentIdentifier containing converters."""
     children: dict = {}
diff --git a/tests/unit/memory/memory_interface/test_interface_scenario_results.py b/tests/unit/memory/memory_interface/test_interface_scenario_results.py
index 4469de670b..f818e45ecd 100644
--- a/tests/unit/memory/memory_interface/test_interface_scenario_results.py
+++ b/tests/unit/memory/memory_interface/test_interface_scenario_results.py
@@ -2,7 +2,6 @@
 # Licensed under the MIT license.
 
 from datetime import datetime, timedelta, timezone
-from typing import Optional
 
 import pytest
 from unit.mocks import get_mock_scorer_identifier
@@ -42,7 +41,7 @@ def create_scenario_result(
     name: str = "Test Scenario",
     description: str = "Test Description",
     version: int = 1,
-    attack_results: Optional[dict[str, list[AttackResult]]] = None,
+    attack_results: dict[str, list[AttackResult]] | None = None,
 ):
     """Helper function to create ScenarioResult."""
     scenario_identifier = ScenarioIdentifier(
diff --git a/tests/unit/mocks.py b/tests/unit/mocks.py
index 2d34d455b5..ffe2fecd9f 100644
--- a/tests/unit/mocks.py
+++ b/tests/unit/mocks.py
@@ -7,7 +7,6 @@
 import uuid
 from collections.abc import Generator, MutableSequence, Sequence
 from contextlib import AbstractAsyncContextManager
-from typing import Optional
 from unittest.mock import MagicMock, patch
 
 from pyrit.memory import AzureSQLMemory, CentralMemory, PromptMemoryEntry
@@ -140,8 +139,8 @@ def set_system_prompt(
         *,
         system_prompt: str,
         conversation_id: str,
-        attack_identifier: Optional[ComponentIdentifier] = None,
-        labels: Optional[dict[str, str]] = None,
+        attack_identifier: ComponentIdentifier | None = None,
+        labels: dict[str, str] | None = None,
     ) -> None:
         self.system_prompt = system_prompt
         if self._memory:
diff --git a/tests/unit/prompt_target/target/test_openai_target_auth.py b/tests/unit/prompt_target/target/test_openai_target_auth.py
index c92614a61d..99cc42fc3e 100644
--- a/tests/unit/prompt_target/target/test_openai_target_auth.py
+++ b/tests/unit/prompt_target/target/test_openai_target_auth.py
@@ -4,7 +4,6 @@
 import asyncio
 import os
 from collections.abc import Callable
-from typing import Optional
 from unittest.mock import AsyncMock, MagicMock, patch
 
 import pytest
@@ -40,8 +39,8 @@ async def _send_prompt_to_target_async(self, *, normalized_conversation):
 def _build_target(
     *,
     endpoint: str = "https://test.openai.azure.com/openai/v1",
-    api_key: Optional[str | Callable] = "test-key",
-    env_vars: Optional[dict[str, str]] = None,
+    api_key: str | Callable | None = "test-key",
+    env_vars: dict[str, str] | None = None,
 ) -> _ConcreteOpenAITarget:
     """Helper to build a _ConcreteOpenAITarget with controlled env."""
     env = {"TEST_MODEL": "gpt-4", "TEST_ENDPOINT": endpoint}
diff --git a/tests/unit/registry/test_scorer_registry.py b/tests/unit/registry/test_scorer_registry.py
index b0d0f3c5d5..6e458ec3eb 100644
--- a/tests/unit/registry/test_scorer_registry.py
+++ b/tests/unit/registry/test_scorer_registry.py
@@ -1,7 +1,6 @@
 # Copyright (c) Microsoft Corporation.
 # Licensed under the MIT license.
 
-from typing import Optional
 
 from pyrit.models import ComponentIdentifier, Message, MessagePiece, Score
 from pyrit.registry.object_registries.scorer_registry import ScorerRegistry
@@ -35,10 +34,10 @@ def _build_identifier(self) -> ComponentIdentifier:
         """
         return self._create_identifier()
 
-    async def _score_async(self, message: Message, *, objective: Optional[str] = None) -> list[Score]:
+    async def _score_async(self, message: Message, *, objective: str | None = None) -> list[Score]:
         return []
 
-    async def _score_piece_async(self, message_piece: MessagePiece, *, objective: Optional[str] = None) -> list[Score]:
+    async def _score_piece_async(self, message_piece: MessagePiece, *, objective: str | None = None) -> list[Score]:
         return []
 
     def validate_return_scores(self, scores: list[Score]):
@@ -59,10 +58,10 @@ def _build_identifier(self) -> ComponentIdentifier:
         """
         return self._create_identifier()
 
-    async def _score_async(self, message: Message, *, objective: Optional[str] = None) -> list[Score]:
+    async def _score_async(self, message: Message, *, objective: str | None = None) -> list[Score]:
         return []
 
-    async def _score_piece_async(self, message_piece: MessagePiece, *, objective: Optional[str] = None) -> list[Score]:
+    async def _score_piece_async(self, message_piece: MessagePiece, *, objective: str | None = None) -> list[Score]:
         return []
 
     def validate_return_scores(self, scores: list[Score]):
@@ -83,16 +82,16 @@ def _build_identifier(self) -> ComponentIdentifier:
         """
         return self._create_identifier()
 
-    async def _score_async(self, message: Message, *, objective: Optional[str] = None) -> list[Score]:
+    async def _score_async(self, message: Message, *, objective: str | None = None) -> list[Score]:
         return []
 
-    async def _score_piece_async(self, message_piece: MessagePiece, *, objective: Optional[str] = None) -> list[Score]:
+    async def _score_piece_async(self, message_piece: MessagePiece, *, objective: str | None = None) -> list[Score]:
         return []
 
     def validate_return_scores(self, scores: list[Score]):
         pass
 
-    def _build_fallback_score(self, *, message: Message, objective: Optional[str]) -> list[Score]:
+    def _build_fallback_score(self, *, message: Message, objective: str | None) -> list[Score]:
         return [
             Score(
                 score_value="false",
diff --git a/tests/unit/score/test_audio_scorer.py b/tests/unit/score/test_audio_scorer.py
index 3b0e51abb4..ca38a8168c 100644
--- a/tests/unit/score/test_audio_scorer.py
+++ b/tests/unit/score/test_audio_scorer.py
@@ -4,7 +4,6 @@
 import os
 import tempfile
 import uuid
-from typing import Optional
 from unittest.mock import AsyncMock, patch
 
 import pytest
@@ -29,7 +28,7 @@ def __init__(self, return_value: bool = True):
     def _build_identifier(self) -> ComponentIdentifier:
         return self._create_identifier()
 
-    async def _score_piece_async(self, message_piece: MessagePiece, *, objective: Optional[str] = None) -> list[Score]:
+    async def _score_piece_async(self, message_piece: MessagePiece, *, objective: str | None = None) -> list[Score]:
         return [
             Score(
                 score_type="true_false",
@@ -56,7 +55,7 @@ def __init__(self, return_value: float = 0.8):
     def _build_identifier(self) -> ComponentIdentifier:
         return self._create_identifier()
 
-    async def _score_piece_async(self, message_piece: MessagePiece, *, objective: Optional[str] = None) -> list[Score]:
+    async def _score_piece_async(self, message_piece: MessagePiece, *, objective: str | None = None) -> list[Score]:
         return [
             Score(
                 score_type="float_scale",
diff --git a/tests/unit/score/test_conversation_history_scorer.py b/tests/unit/score/test_conversation_history_scorer.py
index dc0be088e8..0e957482a2 100644
--- a/tests/unit/score/test_conversation_history_scorer.py
+++ b/tests/unit/score/test_conversation_history_scorer.py
@@ -2,7 +2,6 @@
 # Licensed under the MIT license.
 
 import uuid
-from typing import Optional
 from unittest.mock import AsyncMock, MagicMock
 
 import pytest
@@ -37,7 +36,7 @@ def __init__(self):
     def _build_identifier(self) -> ComponentIdentifier:
         return self._create_identifier()
 
-    async def _score_piece_async(self, message_piece: MessagePiece, *, objective: Optional[str] = None) -> list[Score]:
+    async def _score_piece_async(self, message_piece: MessagePiece, *, objective: str | None = None) -> list[Score]:
         return []
 
 
@@ -50,7 +49,7 @@ def __init__(self):
     def _build_identifier(self) -> ComponentIdentifier:
         return self._create_identifier()
 
-    async def _score_piece_async(self, message_piece: MessagePiece, *, objective: Optional[str] = None) -> list[Score]:
+    async def _score_piece_async(self, message_piece: MessagePiece, *, objective: str | None = None) -> list[Score]:
         return []
 
 
@@ -63,13 +62,13 @@ def __init__(self):
     def _build_identifier(self) -> ComponentIdentifier:
         return self._create_identifier()
 
-    async def _score_piece_async(self, message_piece: MessagePiece, *, objective: Optional[str] = None) -> list[Score]:
+    async def _score_piece_async(self, message_piece: MessagePiece, *, objective: str | None = None) -> list[Score]:
         return []
 
     def validate_return_scores(self, scores: list[Score]):
         pass
 
-    def _build_fallback_score(self, *, message: Message, objective: Optional[str]) -> list[Score]:
+    def _build_fallback_score(self, *, message: Message, objective: str | None) -> list[Score]:
         return [
             Score(
                 score_value="false",
@@ -753,7 +752,7 @@ def _build_identifier(self) -> ComponentIdentifier:
             return self._create_identifier()
 
         async def _score_async(  # type: ignore[override]
-            self, message: Message, *, objective: Optional[str] = None
+            self, message: Message, *, objective: str | None = None
         ) -> list[Score]:
             captured_messages.append(message)
             piece = message.message_pieces[0]
@@ -773,9 +772,7 @@ async def _score_async(  # type: ignore[override]
                 ]
             return []
 
-        async def _score_piece_async(
-            self, message_piece: MessagePiece, *, objective: Optional[str] = None
-        ) -> list[Score]:
+        async def _score_piece_async(self, message_piece: MessagePiece, *, objective: str | None = None) -> list[Score]:
             return []
 
     inner_scorer = HarmfulContentDetector()
diff --git a/tests/unit/score/test_float_scale_score_aggregator.py b/tests/unit/score/test_float_scale_score_aggregator.py
index c726cd331a..19fac4bbff 100644
--- a/tests/unit/score/test_float_scale_score_aggregator.py
+++ b/tests/unit/score/test_float_scale_score_aggregator.py
@@ -1,7 +1,6 @@
 # Copyright (c) Microsoft Corporation.
 # Licensed under the MIT license.
 
-from typing import Optional
 
 from pyrit.models import ComponentIdentifier, Score
 from pyrit.score.float_scale.float_scale_score_aggregator import (
@@ -17,7 +16,7 @@
 )
 
 
-def _mk_score(val: float, *, category: Optional[list[str]] = None, prr_id: str = "1", rationale: str = "") -> Score:
+def _mk_score(val: float, *, category: list[str] | None = None, prr_id: str = "1", rationale: str = "") -> Score:
     """Helper to create a float scale score."""
     return Score(
         score_value=str(val),
diff --git a/tests/unit/score/test_float_scale_threshold_scorer.py b/tests/unit/score/test_float_scale_threshold_scorer.py
index de91ff5d62..b98cb183d8 100644
--- a/tests/unit/score/test_float_scale_threshold_scorer.py
+++ b/tests/unit/score/test_float_scale_threshold_scorer.py
@@ -2,7 +2,6 @@
 # Licensed under the MIT license.
 
 import uuid
-from typing import Optional
 from unittest.mock import AsyncMock, MagicMock, patch
 
 import pytest
@@ -237,9 +236,7 @@ def __init__(self):
         def _build_identifier(self) -> ComponentIdentifier:
             return self._create_identifier()
 
-        async def _score_piece_async(
-            self, message_piece: MessagePiece, *, objective: Optional[str] = None
-        ) -> list[Score]:
+        async def _score_piece_async(self, message_piece: MessagePiece, *, objective: str | None = None) -> list[Score]:
             return [
                 Score(
                     score_value="0.9",
diff --git a/tests/unit/score/test_gandalf_scorer.py b/tests/unit/score/test_gandalf_scorer.py
index 13ecaeed06..e47a4c39cd 100644
--- a/tests/unit/score/test_gandalf_scorer.py
+++ b/tests/unit/score/test_gandalf_scorer.py
@@ -2,7 +2,6 @@
 # Licensed under the MIT license.
 
 import uuid
-from typing import Optional
 from unittest.mock import AsyncMock, MagicMock, patch
 
 import pytest
@@ -15,7 +14,7 @@
 from pyrit.score import GandalfScorer
 
 
-def generate_password_extraction_response(response_text: str, conversation_id: Optional[str] = None) -> Message:
+def generate_password_extraction_response(response_text: str, conversation_id: str | None = None) -> Message:
     return Message(
         message_pieces=[
             MessagePiece(
@@ -30,7 +29,7 @@ def generate_password_extraction_response(response_text: str, conversation_id: O
     )
 
 
-def generate_request(conversation_id: Optional[str] = None) -> Message:
+def generate_request(conversation_id: str | None = None) -> Message:
     return Message(
         message_pieces=[
             MessagePiece(
diff --git a/tests/unit/score/test_scorer.py b/tests/unit/score/test_scorer.py
index 8996ebdb6a..aaf1b964f7 100644
--- a/tests/unit/score/test_scorer.py
+++ b/tests/unit/score/test_scorer.py
@@ -4,7 +4,6 @@
 import asyncio
 import uuid
 from textwrap import dedent
-from typing import Optional
 from unittest.mock import AsyncMock, MagicMock, patch
 
 import pytest
@@ -66,7 +65,7 @@ def _build_identifier(self) -> ComponentIdentifier:
         """Build the scorer evaluation identifier for this mock scorer."""
         return self._create_identifier()
 
-    async def _score_async(self, message: Message, *, objective: Optional[str] = None) -> list[Score]:
+    async def _score_async(self, message: Message, *, objective: str | None = None) -> list[Score]:
         return [
             Score(
                 score_value="true",
@@ -81,7 +80,7 @@ async def _score_async(self, message: Message, *, objective: Optional[str] = Non
             )
         ]
 
-    async def _score_piece_async(self, message_piece: MessagePiece, *, objective: Optional[str] = None) -> list[Score]:
+    async def _score_piece_async(self, message_piece: MessagePiece, *, objective: str | None = None) -> list[Score]:
         return [
             Score(
                 score_value="true",
@@ -122,7 +121,7 @@ def _build_identifier(self) -> ComponentIdentifier:
         """Build the scorer evaluation identifier for this mock scorer."""
         return self._create_identifier()
 
-    async def _score_piece_async(self, message_piece: MessagePiece, *, objective: Optional[str] = None) -> list[Score]:
+    async def _score_piece_async(self, message_piece: MessagePiece, *, objective: str | None = None) -> list[Score]:
         # Track which pieces get scored
         self.scored_piece_ids.append(str(message_piece.id))
 
@@ -144,7 +143,7 @@ def validate_return_scores(self, scores: list[Score]):
         for score in scores:
             assert 0 <= float(score.score_value) <= 1
 
-    def _build_fallback_score(self, *, message: Message, objective: Optional[str]) -> list[Score]:
+    def _build_fallback_score(self, *, message: Message, objective: str | None) -> list[Score]:
         return [
             Score(
                 score_value="0.0",
@@ -1168,9 +1167,7 @@ def _build_identifier(self) -> ComponentIdentifier:
             """Build the scorer evaluation identifier for this test scorer."""
             return self._create_identifier()
 
-        async def _score_piece_async(
-            self, message_piece: MessagePiece, *, objective: Optional[str] = None
-        ) -> list[Score]:
+        async def _score_piece_async(self, message_piece: MessagePiece, *, objective: str | None = None) -> list[Score]:
             self.scored_piece_ids.append(message_piece.id)
             return [
                 Score(
@@ -1355,7 +1352,7 @@ def _build_identifier(self) -> ComponentIdentifier:
                 return self._create_identifier()
 
             async def _score_piece_async(
-                self, message_piece: MessagePiece, *, objective: Optional[str] = None
+                self, message_piece: MessagePiece, *, objective: str | None = None
             ) -> list[Score]:
                 # Return empty list to simulate no scorable pieces
                 return []
@@ -1482,7 +1479,7 @@ def _build_identifier(self) -> ComponentIdentifier:
                 return self._create_identifier()
 
             async def _score_piece_async(
-                self, message_piece: MessagePiece, *, objective: Optional[str] = None
+                self, message_piece: MessagePiece, *, objective: str | None = None
             ) -> list[Score]:
                 return []
 
@@ -1622,7 +1619,7 @@ async def test_score_value_with_llm_skips_reasoning_piece(good_json):
 class _AcceptAllValidator(ScorerPromptValidator):
     """Validator that accepts all pieces (like SelfAskRefusalScorer's default)."""
 
-    def validate(self, message: Message, objective: Optional[str] = None) -> None:
+    def validate(self, message: Message, objective: str | None = None) -> None:
         pass
 
     def is_message_piece_supported(self, message_piece: MessagePiece) -> bool:
@@ -1635,21 +1632,21 @@ class _TextOnlyValidator(ScorerPromptValidator):
     def __init__(self) -> None:
         super().__init__(supported_data_types=["text", "image_path"])
 
-    def validate(self, message: Message, objective: Optional[str] = None) -> None:
+    def validate(self, message: Message, objective: str | None = None) -> None:
         pass
 
 
 class _BlockedContentScorer(TrueFalseScorer):
     """A mock TrueFalseScorer that records what pieces it was asked to score."""
 
-    def __init__(self, *, validator: Optional[ScorerPromptValidator] = None) -> None:
+    def __init__(self, *, validator: ScorerPromptValidator | None = None) -> None:
         super().__init__(validator=validator or _TextOnlyValidator())
         self.scored_pieces: list[MessagePiece] = []
 
     def _build_identifier(self) -> ComponentIdentifier:
         return self._create_identifier()
 
-    async def _score_piece_async(self, message_piece: MessagePiece, *, objective: Optional[str] = None) -> list[Score]:
+    async def _score_piece_async(self, message_piece: MessagePiece, *, objective: str | None = None) -> list[Score]:
         self.scored_pieces.append(message_piece)
         return [
             Score(
@@ -1676,7 +1673,7 @@ def __init__(self) -> None:
     def _build_identifier(self) -> ComponentIdentifier:
         return self._create_identifier()
 
-    async def _score_piece_async(self, message_piece: MessagePiece, *, objective: Optional[str] = None) -> list[Score]:
+    async def _score_piece_async(self, message_piece: MessagePiece, *, objective: str | None = None) -> list[Score]:
         self.scored_pieces.append(message_piece)
         if message_piece.response_error == "blocked":
             return [
@@ -1707,7 +1704,7 @@ async def _score_piece_async(self, message_piece: MessagePiece, *, objective: Op
         ]
 
 
-def _make_blocked_piece(*, partial_content: Optional[str] = None, conversation_id: str = "test-convo") -> MessagePiece:
+def _make_blocked_piece(*, partial_content: str | None = None, conversation_id: str = "test-convo") -> MessagePiece:
     """Create a blocked MessagePiece, optionally with partial content metadata."""
     metadata: dict = {}
     if partial_content is not None:
diff --git a/tests/unit/score/test_true_false_composite_scorer.py b/tests/unit/score/test_true_false_composite_scorer.py
index af11b5e045..e82aeba9c5 100644
--- a/tests/unit/score/test_true_false_composite_scorer.py
+++ b/tests/unit/score/test_true_false_composite_scorer.py
@@ -1,7 +1,6 @@
 # Copyright (c) Microsoft Corporation.
 # Licensed under the MIT license.
 
-from typing import Optional
 from unittest.mock import MagicMock
 
 import pytest
@@ -46,7 +45,7 @@ def _build_identifier(self) -> ComponentIdentifier:
         """
         return self._create_identifier()
 
-    async def _score_piece_async(self, message_piece: MessagePiece, *, objective: Optional[str] = None) -> list[Score]:
+    async def _score_piece_async(self, message_piece: MessagePiece, *, objective: str | None = None) -> list[Score]:
         return [
             Score(
                 score_value=str(self._score_value),
@@ -154,9 +153,7 @@ def __init__(self):
         def _build_identifier(self) -> ComponentIdentifier:
             return self._create_identifier()
 
-        async def _score_piece_async(
-            self, message_piece: MessagePiece, *, objective: Optional[str] = None
-        ) -> list[Score]:
+        async def _score_piece_async(self, message_piece: MessagePiece, *, objective: str | None = None) -> list[Score]:
             return []
 
     with pytest.raises(ValueError, match="All scorers must be true_false scorers"):
diff --git a/tests/unit/score/test_video_scorer.py b/tests/unit/score/test_video_scorer.py
index 4c5d4d3524..28dcbba779 100644
--- a/tests/unit/score/test_video_scorer.py
+++ b/tests/unit/score/test_video_scorer.py
@@ -3,7 +3,6 @@
 
 import os
 import uuid
-from typing import Optional
 from unittest.mock import AsyncMock, MagicMock, patch
 
 import numpy as np
@@ -74,7 +73,7 @@ def _build_identifier(self) -> ComponentIdentifier:
         """
         return self._create_identifier()
 
-    async def _score_piece_async(self, message_piece: MessagePiece, *, objective: Optional[str] = None) -> list[Score]:
+    async def _score_piece_async(self, message_piece: MessagePiece, *, objective: str | None = None) -> list[Score]:
         return [
             Score(
                 score_type="true_false",
@@ -106,7 +105,7 @@ def _build_identifier(self) -> ComponentIdentifier:
         """
         return self._create_identifier()
 
-    async def _score_piece_async(self, message_piece: MessagePiece, *, objective: Optional[str] = None) -> list[Score]:
+    async def _score_piece_async(self, message_piece: MessagePiece, *, objective: str | None = None) -> list[Score]:
         return [
             Score(
                 score_type="float_scale",
@@ -295,7 +294,7 @@ def __init__(self, return_value: bool = True):
     def _build_identifier(self) -> ComponentIdentifier:
         return self._create_identifier()
 
-    async def _score_piece_async(self, message_piece: MessagePiece, *, objective: Optional[str] = None) -> list[Score]:
+    async def _score_piece_async(self, message_piece: MessagePiece, *, objective: str | None = None) -> list[Score]:
         self.received_objective = objective
         return [
             Score(