diff --git a/src/etc/debugger_tester/lldb/batchmode.py b/src/etc/debugger_tester/lldb/batchmode.py
index fdf6a34c01716..ebc7b7ff91577 100644
--- a/src/etc/debugger_tester/lldb/batchmode.py
+++ b/src/etc/debugger_tester/lldb/batchmode.py
@@ -16,6 +16,7 @@
 import _thread as thread
 import os
 import re
+import signal
 import sys
 import threading
 import time
@@ -184,6 +185,27 @@ def dispatch_repr(var_name: str, breakpoint_index: int, frame: lldb.SBFrame) ->
     return check(var_name, breakpoint_index, frame) == Result.Ok
 
 
+def quit_with_error(debugger: lldb.SBDebugger):
+    """Kills the parent LLDB process with a non-0 exit code"""
+
+    # file handles aren't guaranteed to be flushed when python doesn't return control back to LLDB,
+    # so we need to do it manually
+    debugger.GetOutputFile().Flush()
+    debugger.GetErrorFile().Flush()
+    sys.stdout.flush()
+    sys.stderr.flush()
+
+    # When using a debugger created from the python script (e.g. `lldb.SBDebugger.Create()`), this
+    # doesn't actually work, but it doesn't hurt to try =)
+    debugger.HandleCommand("quit 1")
+
+    # Returning status codes using `sys.exit` doesn't work since we're in an LLDB managed python
+    # instance. Instead, we kill the PID, which happens to be the parent LLDB process.
+    # Note: We use SIGTERM because it works on linux and windows, unlike SIGKILL, and doesn't cause
+    # LLDB to spit out a backtrace like SIGABRT.
+    os.kill(os.getpid(), signal.SIGTERM)
+
+
 ####################################################################################################
 # ~main
 ####################################################################################################
@@ -203,12 +225,12 @@ def main():
     # Start the timeout watchdog
     start_watchdog()
 
-    # This is the debugger instance of the lldb executable that imported and ran this python script.
-    # There is some weird behavior around LLDB reassigning, clearing, or not updating their own
-    # references (like `lldb.debugger`) while a python function is actively running (i.e. if control
-    # is not given back to the REPL). To prevent LLDB from changing things out from under us, we
-    # store this reference locally.
-    debugger = lldb.debugger
+    # We use a new `SBDebugger` instance, since LLDB often doesn't update internal state/python
+    # state while a command is being run. Since the entirety of `batchmode` is executed via a
+    # `script` command, the parent LLDB never gets a chance to update.
+    # In LLDB <23 this was less of an issue, but a change in LLDB 23 made it difficult to create
+    # targets from the parent debugger instance.
+    debugger = lldb.SBDebugger.Create()
 
     # When we step or continue, don't return from the function until the process
     # stops. We do this by setting the async mode to false.
@@ -283,13 +305,10 @@ def main():
         print(f"Could not read debugging script '{script_path}'.")
         traceback.print_exception(type(e), e, e.__traceback__, file=sys.stdout)
         print("Aborting.")
-        # Returning status codes using `sys.exit` doesn't work since we're in an LLDB managed python
-        # instance. This command sets the exit code but *does not* kill LLDB, the debugee process,
-        # or the SBDebugger object.
-        debugger.HandleCommand("quit 1")
+        quit_with_error(debugger)
     except Exception as e:
         traceback.print_exception(type(e), e, e.__traceback__, file=sys.stdout)
-        debugger.HandleCommand("quit 1")
+        quit_with_error(debugger)
     else:  # Executes if the `try` block throws no exceptions.
         if repr_cmd_run:
             # We save importing these until we actually see a repr command. This prevents us
@@ -329,7 +348,7 @@ def main():
                 )
 
             if not tested_all_types() or not tested_all_variables():
-                debugger.HandleCommand("quit 1")
+                quit_with_error(debugger)
             elif BLESS:
                 from lldb_providers import FEATURE_FLAGS