diff --git a/apps/server/src/provider/Drivers/PiDriver.test.ts b/apps/server/src/provider/Drivers/PiDriver.test.ts
new file mode 100644
index 000000000000..7202f1784a8e
--- /dev/null
+++ b/apps/server/src/provider/Drivers/PiDriver.test.ts
@@ -0,0 +1,219 @@
+import * as NodeServices from "@effect/platform-node/NodeServices";
+import { assert, it } from "@effect/vitest";
+import { ProviderInstanceId, type PiSettings } from "@t3tools/contracts";
+import * as Deferred from "effect/Deferred";
+import * as Effect from "effect/Effect";
+import * as Fiber from "effect/Fiber";
+import * as Layer from "effect/Layer";
+import * as Queue from "effect/Queue";
+import * as Schema from "effect/Schema";
+import * as Sink from "effect/Sink";
+import * as Stream from "effect/Stream";
+import * as TestClock from "effect/testing/TestClock";
+import { HttpClient } from "effect/http";
+import { ChildProcess, ChildProcessSpawner } from "effect/process";
+
+import * as BackgroundPolicy from "../../background/BackgroundPolicy.ts";
+import * as ServerConfig from "../../config.ts";
+import * as IdAllocator from "../../orchestration-v2/IdAllocator.ts";
+import * as ServerSettings from "../../serverSettings.ts";
+import { PiDriver } from "./PiDriver.ts";
+
+const layerTest = Layer.mergeAll(
+  ServerConfig.layerTest("/machine", { prefix: "t3-pi-driver-" }),
+  IdAllocator.layer,
+  ServerSettings.layerTest({ enableProviderUpdateChecks: false }),
+  Layer.mock(BackgroundPolicy.BackgroundPolicy)({
+    shouldRunScopeWork: () => Effect.succeed(false),
+  }),
+  Layer.succeed(
+    HttpClient.HttpClient,
+    HttpClient.make(() => Effect.die("Unexpected HTTP")),
+  ),
+).pipe(Layer.provideMerge(NodeServices.layer));
+
+const decodeRequest = Schema.decodeSync(
+  Schema.fromJsonString(Schema.Record(Schema.String, Schema.Unknown)),
+);
+const encoder = new TextEncoder();
+const personalSkill = {
+  name: "skill:personal",
+  source: "skill",
+  sourceInfo: { scope: "user", path: "/home/.pi/agent/skills/personal/SKILL.md" },
+};
+
+// Respond through the real stdio transport, with a distinct command catalog for each cwd.
+const makePiSpawner = Effect.gen(function* () {
+  const pendingCommand = yield* Deferred.make<void>();
+  const launches: Array<ChildProcess.StandardCommand> = [];
+  const spawner = ChildProcessSpawner.make((command) =>
+    Effect.gen(function* () {
+      assert.isTrue(ChildProcess.isStandardCommand(command));
+      if (!ChildProcess.isStandardCommand(command)) return yield* Effect.die("Unexpected pipeline");
+      launches.push(command);
+      const version = command.args.includes("--version");
+      const stdout = yield* Queue.unbounded<Uint8Array>();
+      const cwd = command.options.cwd;
+      return ChildProcessSpawner.makeHandle({
+        // Outside the valid PID range, so transport cleanup cannot signal a real process.
+        pid: ChildProcessSpawner.ProcessId(999_999_999),
+        exitCode: version ? Effect.succeed(ChildProcessSpawner.ExitCode(0)) : Effect.never,
+        isRunning: Effect.succeed(!version),
+        kill: () => Effect.void,
+        unref: Effect.succeed(Effect.void),
+        stdin: Sink.forEach((chunk: Uint8Array) => {
+          const request = decodeRequest(new TextDecoder().decode(chunk).trim());
+          if (cwd === "/pending" && request.type === "get_commands") {
+            return Deferred.succeed(pendingCommand, undefined).pipe(Effect.asVoid);
+          }
+          const failed = cwd === "/failed" && request.type === "get_commands";
+          const data =
+            request.type === "get_commands"
+              ? {
+                  commands: [
+                    personalSkill,
+                    ...(cwd === "/machine"
+                      ? []
+                      : [
+                          {
+                            name: `skill:${cwd?.slice(1)}`,
+                            source: "skill",
+                            sourceInfo: {
+                              scope: "project",
+                              path: `${cwd}/.agents/skills/SKILL.md`,
+                            },
+                          },
+                          { name: `prompt-${cwd?.slice(1)}`, source: "prompt" },
+                        ]),
+                  ],
+                }
+              : request.type === "get_available_models"
+                ? { models: [{ provider: "test", id: "model" }] }
+                : {};
+          return Queue.offer(
+            stdout,
+            encoder.encode(
+              `${JSON.stringify({ type: "response", id: request.id, success: !failed, data, ...(failed ? { error: "commands unavailable" } : {}) })}\n`,
+            ),
+          ).pipe(Effect.asVoid);
+        }),
+        stdout: version ? Stream.succeed(encoder.encode("pi 1.0.2\n")) : Stream.fromQueue(stdout),
+        stderr: Stream.empty,
+        all: Stream.empty,
+        getInputFd: () => Sink.drain,
+        getOutputFd: () => Stream.empty,
+      });
+    }),
+  );
+  return { spawner, launches, pendingCommand };
+});
+
+const create = (config: Partial<PiSettings> = {}, enabled = true) =>
+  PiDriver.create({
+    instanceId: ProviderInstanceId.make("pi-workspace-test"),
+    displayName: "My Pi",
+    accentColor: "#abcdef",
+    environment: [{ name: "PI_CODING_AGENT_DIR", value: "/isolated-pi", sensitive: false }],
+    enabled,
+    config: { ...PiDriver.defaultConfig(), binaryPath: "custom-pi", ...config },
+  });
+
+it.layer(layerTest)("PiDriver workspace discovery", (it) => {
+  it.effect("keeps each workspace's skills and commands separate from the machine catalog", () =>
+    Effect.gen(function* () {
+      const { spawner, launches } = yield* makePiSpawner;
+      const instance = yield* create({ launchArgs: '--approve --skill "extra skill"' }).pipe(
+        Effect.provideService(ChildProcessSpawner.ChildProcessSpawner, spawner),
+      );
+      yield* instance.snapshot.refresh;
+      assert.isDefined(instance.snapshotForCwd);
+      const [first, second] = yield* Effect.all(
+        [instance.snapshotForCwd!("/first"), instance.snapshotForCwd!("/second")],
+        { concurrency: "unbounded" },
+      );
+      assert.deepEqual(
+        first.skills.map((skill) => skill.name),
+        ["personal", "first"],
+      );
+      assert.deepEqual(
+        second.skills.map((skill) => skill.name),
+        ["personal", "second"],
+      );
+      assert.deepEqual(
+        first.slashCommands.map((command) => command.name),
+        ["compact", "prompt-first"],
+      );
+      const machine = yield* instance.snapshot.getSnapshot;
+      assert.deepEqual(
+        machine.skills.map((skill) => skill.name),
+        ["personal"],
+      );
+      assert.deepEqual(
+        machine.slashCommands.map((command) => command.name),
+        ["compact"],
+      );
+      assert.equal(first.instanceId, instance.instanceId);
+      assert.equal(first.displayName, "My Pi");
+      assert.equal(first.accentColor, "#abcdef");
+      assert.deepEqual(first.models, machine.models);
+      const workspaceLaunch = launches.find((launch) => launch.options.cwd === "/first");
+      assert.isDefined(workspaceLaunch);
+      assert.equal(workspaceLaunch!.command, "custom-pi");
+      assert.includeMembers(
+        [...workspaceLaunch!.args],
+        ["--approve", "--skill", "extra skill", "--no-session"],
+      );
+      assert.equal(workspaceLaunch!.options.env?.PI_CODING_AGENT_DIR, "/isolated-pi");
+    }).pipe(Effect.scoped),
+  );
+
+  it.effect("does not run a disabled provider's workspace probe", () =>
+    Effect.gen(function* () {
+      const instance = yield* create({}, false).pipe(
+        Effect.provideService(
+          ChildProcessSpawner.ChildProcessSpawner,
+          ChildProcessSpawner.make(() => Effect.die("Disabled Pi must not spawn")),
+        ),
+      );
+      assert.isDefined(instance.snapshotForCwd);
+      const workspace = yield* instance.snapshotForCwd!("/first");
+      assert.isFalse(workspace.enabled);
+      assert.deepEqual(workspace.skills, []);
+    }).pipe(Effect.scoped),
+  );
+
+  it.effect(
+    "fails command discovery instead of returning an empty successful workspace catalog",
+    () =>
+      Effect.gen(function* () {
+        const { spawner } = yield* makePiSpawner;
+        const instance = yield* create().pipe(
+          Effect.provideService(ChildProcessSpawner.ChildProcessSpawner, spawner),
+        );
+        yield* instance.snapshot.refresh;
+        assert.isDefined(instance.snapshotForCwd);
+        const error = yield* Effect.flip(instance.snapshotForCwd!("/failed"));
+        assert.equal(error._tag, "ProviderDriverError");
+        assert.equal(error.instanceId, instance.instanceId);
+        assert.deepEqual(
+          (yield* instance.snapshot.getSnapshot).skills.map((skill) => skill.name),
+          ["personal"],
+        );
+      }).pipe(Effect.scoped),
+  );
+
+  it.effect("times out workspace discovery that needs interactive input", () =>
+    Effect.gen(function* () {
+      const { spawner, pendingCommand } = yield* makePiSpawner;
+      const instance = yield* create().pipe(
+        Effect.provideService(ChildProcessSpawner.ChildProcessSpawner, spawner),
+      );
+      const probe = yield* instance.snapshotForCwd!("/pending").pipe(Effect.flip, Effect.forkChild);
+      yield* Deferred.await(pendingCommand);
+      yield* TestClock.adjust("15 seconds");
+      const error = yield* Fiber.join(probe);
+      assert.equal(error._tag, "ProviderDriverError");
+      assert.include(error.detail, "workspace commands");
+    }).pipe(Effect.scoped),
+  );
+});
diff --git a/apps/server/src/provider/Drivers/PiDriver.ts b/apps/server/src/provider/Drivers/PiDriver.ts
index 07c33753874a..9a7ec6320b7d 100644
--- a/apps/server/src/provider/Drivers/PiDriver.ts
+++ b/apps/server/src/provider/Drivers/PiDriver.ts
@@ -26,6 +26,7 @@ import { ProviderDriverError } from "../Errors.ts";
 import {
   buildInitialPiProviderSnapshot,
   checkPiProviderStatus,
+  discoverPiCommandsForCwd,
   enrichPiSnapshot,
 } from "../PiProvider.ts";
 import { makeManagedServerProvider } from "../makeManagedServerProvider.ts";
@@ -188,6 +189,26 @@ export const PiDriver: ProviderDriver<PiSettings, PiDriverEnv> = {
         accentColor,
         enabled,
         snapshot,
+        snapshotForCwd: (workspaceCwd) =>
+          !effectiveConfig.enabled
+            ? snapshot.getSnapshot
+            : Effect.all([
+                snapshot.getSnapshot,
+                discoverPiCommandsForCwd(effectiveConfig, processEnv, workspaceCwd).pipe(
+                  Effect.provideService(ChildProcessSpawner.ChildProcessSpawner, spawner),
+                  Effect.mapError(
+                    (cause) =>
+                      new ProviderDriverError({
+                        driver: DRIVER_KIND,
+                        instanceId,
+                        detail: "Failed to discover Pi workspace commands.",
+                        cause,
+                      }),
+                  ),
+                ),
+              ]).pipe(
+                Effect.map(([machineSnapshot, commands]) => ({ ...machineSnapshot, ...commands })),
+              ),
         orchestrationAdapter,
         textGeneration,
       } satisfies ProviderInstance;
diff --git a/apps/server/src/provider/PiProvider.ts b/apps/server/src/provider/PiProvider.ts
index ec785b85a33b..2aaf9ab72e8d 100644
--- a/apps/server/src/provider/PiProvider.ts
+++ b/apps/server/src/provider/PiProvider.ts
@@ -32,6 +32,8 @@ import {
 } from "../orchestration-v2/Adapters/piT3McpInjection.ts";
 import {
   makePiRpcConnection,
+  PiRpcError,
+  PiRpcTimeoutError,
   piRecordField as recordField,
   piRecordString as recordString,
 } from "../orchestration-v2/Adapters/PiRpc.ts";
@@ -126,6 +128,33 @@ function parseDiscoveredModels(
   return parsed;
 }
 
+const makePiDiscoveryConnection = Effect.fnUntraced(function* (
+  piSettings: PiSettings,
+  environment: NodeJS.ProcessEnv,
+  launchArgs: ReadonlyArray<string>,
+  cwd?: string,
+) {
+  const launch = buildPiRpcLaunch({
+    launchArgs,
+    environment,
+    mcpSession: undefined,
+    extensionPath: undefined,
+    ephemeral: true,
+  });
+  const connection = yield* makePiRpcConnection({
+    command: piSettings.binaryPath || "pi",
+    args: launch.args,
+    cwd,
+    env: launch.env,
+  });
+  yield* Stream.fromQueue(connection.events).pipe(
+    Stream.runDrain,
+    Effect.ignore,
+    Effect.forkScoped,
+  );
+  return connection;
+});
+
 const discoverPiViaRpc = (
   piSettings: PiSettings,
   environment: NodeJS.ProcessEnv,
@@ -133,24 +162,7 @@ const discoverPiViaRpc = (
   cwd?: string,
 ) =>
   Effect.gen(function* () {
-    const launch = buildPiRpcLaunch({
-      launchArgs,
-      environment,
-      mcpSession: undefined,
-      extensionPath: undefined,
-      ephemeral: true,
-    });
-    const connection = yield* makePiRpcConnection({
-      command: piSettings.binaryPath || "pi",
-      args: launch.args,
-      cwd,
-      env: launch.env,
-    });
-    yield* Stream.fromQueue(connection.events).pipe(
-      Stream.runDrain,
-      Effect.ignore,
-      Effect.forkScoped,
-    );
+    const connection = yield* makePiDiscoveryConnection(piSettings, environment, launchArgs, cwd);
     const stateData = yield* connection.request({ type: "get_state" });
     const modelsData = yield* connection.request({ type: "get_available_models" });
     const commandsData = yield* connection
@@ -169,6 +181,34 @@ const discoverPiViaRpc = (
     } satisfies PiDiscovery;
   }).pipe(Effect.scoped);
 
+/** Probe the full command catalog Pi exposes in a workspace without changing machine health. */
+export const discoverPiCommandsForCwd = Effect.fn("discoverPiCommandsForCwd")(
+  function* (piSettings: PiSettings, environment: NodeJS.ProcessEnv, cwd: string) {
+    const launchArgs = resolvePiLaunchArgs(piSettings.launchArgs);
+    if (!launchArgs.ok) {
+      return yield* new PiRpcError({ operation: "launch", detail: launchArgs.message });
+    }
+    const connection = yield* makePiDiscoveryConnection(
+      piSettings,
+      environment,
+      launchArgs.args,
+      cwd,
+    );
+    // A failed read must not replace a previously usable workspace catalog with an empty one.
+    const commandsData = yield* connection.request({ type: "get_commands" });
+    const { slashCommands, skills } = parsePiDiscoveredCommands(commandsData);
+    return { slashCommands: withPiBuiltinSlashCommands(slashCommands), skills };
+  },
+  Effect.scoped,
+  Effect.timeoutOrElse({
+    duration: PI_RPC_DISCOVERY_TIMEOUT_MS,
+    orElse: () =>
+      Effect.fail(
+        new PiRpcTimeoutError({ operation: "discovery", timeoutMs: PI_RPC_DISCOVERY_TIMEOUT_MS }),
+      ),
+  }),
+);
+
 const runPiVersionCommand = (piSettings: PiSettings, environment: NodeJS.ProcessEnv) =>
   Effect.gen(function* () {
     const command = piSettings.binaryPath || "pi";