diff --git a/packages/ui/src/sync/DOCUMENTATION.md b/packages/ui/src/sync/DOCUMENTATION.md
index 420004a2..349e10d7 100644
--- a/packages/ui/src/sync/DOCUMENTATION.md
+++ b/packages/ui/src/sync/DOCUMENTATION.md
@@ -257,6 +257,10 @@ Examples of global-store updates performed in `session-actions.ts`:
 - `deleteSession()` / `deleteSessions()` -> wait for server confirmation or `404`, then remove the session and its persisted state
 - `moveSessionToDirectory()` -> move the session between directory stores and update the global directory index
 
+### Blocking-request (question/permission) reply routing
+
+`respondToQuestion`, `rejectQuestion`, `respondToPermission`, and `dismissPermission` route the reply through `resolveDirectoryForBlockingRequest`. The directory chosen decides which OpenCode instance resolves the pending request, so it must be the **session record's own server-confirmed directory** (ownership), never the containing child-store key (containment): a project store legitimately holds its worktree sessions, and a reply addressed to the parent instance makes the server answer `QuestionNotFoundError` while the question stays pending in the worktree instance — the session is then stuck on the running question tool with no recovery. When a reply/reject comes back not-found, the stale request is removed locally and a `settled-running-tool` tail materialization is enqueued so the trailing tool part converges to the server's actual state instead of leaving the UI on "asking question" forever.
+
 ### Restore (unarchive) contract
 
 The OpenCode server cannot clear `time.archived` over HTTP: `session.update`
diff --git a/packages/ui/src/sync/session-actions.test.ts b/packages/ui/src/sync/session-actions.test.ts
index 84c276f8..d815b6dd 100644
--- a/packages/ui/src/sync/session-actions.test.ts
+++ b/packages/ui/src/sync/session-actions.test.ts
@@ -1461,6 +1461,165 @@ describe("rejectQuestion passes directory", () => {
   })
 })
 
+describe("blocking request reply routing and stale recovery (issue OPE-236)", () => {
+  const materializationCalls: Array<{ directory: string; sessionID: string; messageID: string }> = []
+  const enqueueMaterialization = (directory: string, sessionID: string, messageID: string) => {
+    materializationCalls.push({ directory, sessionID, messageID })
+  }
+
+  beforeEach(() => {
+    replyCalls.length = 0
+    scopedClientDirectories.length = 0
+    questionReplyError = null
+    questionRejectError = null
+    materializationCalls.length = 0
+  })
+
+  test("routes the question reply by the request's own session directory, not the containing store key", async () => {
+    // The question was asked by a worktree session whose record lives in the
+    // parent store (containment). The reply must be addressed to the session's
+    // own server-confirmed directory — otherwise the server resolves the
+    // parent instance, does not find the pending question, and answers
+    // QuestionNotFoundError, leaving the session stuck on "asking question".
+    const question = buildQuestion("q-wt", "session-wt")
+    const store = createStore({}, {
+      session: [{ id: "session-wt", directory: "/test/project/wt" } as Session],
+      question: { "session-wt": [question] },
+    })
+    const childStores = createChildStores([["/test/project", store]])
+
+    const { setActionRefs, respondToQuestion } = await import("./session-actions")
+    setActionRefs(mockSdk as unknown as OpencodeClient, childStores, () => "/test/project", enqueueMaterialization)
+
+    await respondToQuestion("session-wt", "q-wt", [["Yes"]])
+
+    expect(scopedClientDirectories).toEqual(["/test/project/wt"])
+    expect(replyCalls[0]?.params.directory).toBe("/test/project/wt")
+    expect(replyCalls[0]?.params.requestID).toBe("q-wt")
+  })
+
+  test("routes permission replies by the request's own session directory", async () => {
+    const permission = buildPermission("perm-wt", "session-wt")
+    const store = createStore(
+      { "session-wt": [permission] },
+      {
+        session: [{ id: "session-wt", directory: "/test/project/wt" } as Session],
+      },
+    )
+    const childStores = createChildStores([["/test/project", store]])
+
+    const { setActionRefs, respondToPermission } = await import("./session-actions")
+    setActionRefs(mockSdk as unknown as OpencodeClient, childStores, () => "/test/project", enqueueMaterialization)
+
+    await respondToPermission("session-wt", "perm-wt", "once")
+
+    expect(scopedClientDirectories).toEqual(["/test/project/wt"])
+    expect(replyCalls[0]?.params.directory).toBe("/test/project/wt")
+    expect(replyCalls[0]?.params.requestID).toBe("perm-wt")
+  })
+
+  test("falls back to the containing store key when the session record carries no directory", async () => {
+    const question = buildQuestion("q-1", "session-a")
+    const store = createStore({}, {
+      session: [{ id: "session-a" } as Session],
+      question: { "session-a": [question] },
+    })
+    const childStores = createChildStores([["/test/project", store]])
+
+    const { setActionRefs, respondToQuestion } = await import("./session-actions")
+    setActionRefs(mockSdk as unknown as OpencodeClient, childStores, () => "/test/project", enqueueMaterialization)
+
+    await respondToQuestion("session-a", "q-1", [["Yes"]])
+
+    expect(scopedClientDirectories).toEqual(["/test/project"])
+    expect(replyCalls[0]?.params.directory).toBe("/test/project")
+  })
+
+  test("enqueues settled-running-tool tail recovery when the question reply is not found", async () => {
+    const question = buildQuestion("q-stale", "session-a")
+    const store = createStore({}, {
+      session: [{ id: "session-a" } as Session],
+      question: { "session-a": [question] },
+      message: {
+        "session-a": [{ id: "msg-1", sessionID: "session-a", role: "assistant", time: { created: 1 } } as Message],
+      },
+      part: {
+        "msg-1": [{
+          id: "prt-1",
+          messageID: "msg-1",
+          sessionID: "session-a",
+          type: "tool",
+          tool: "question",
+          state: { status: "running" },
+        } as Part],
+      },
+    })
+    const childStores = createChildStores([["/test/project", store]])
+    questionReplyError = Object.assign(new Error("question.reply failed (404): QuestionNotFoundError"), { status: 404 })
+
+    const { setActionRefs, respondToQuestion } = await import("./session-actions")
+    setActionRefs(mockSdk as unknown as OpencodeClient, childStores, () => "/test/project", enqueueMaterialization)
+
+    let thrown: unknown
+    try {
+      await respondToQuestion("session-a", "q-stale", [["Yes"]])
+    } catch (error) {
+      thrown = error
+    }
+
+    expect(thrown).toBeInstanceOf(Error)
+    // The stale request is gone from the store and the trailing running tool
+    // part is reconciled instead of leaving the UI stuck on "asking question".
+    expect(store.getState().question["session-a"]).toBe(undefined)
+    expect(materializationCalls).toEqual([{ directory: "/test/project", sessionID: "session-a", messageID: "msg-1" }])
+  })
+
+  test("enqueues tail recovery on reject not-found but not on success", async () => {
+    const question = buildQuestion("q-1", "session-a")
+    const store = createStore({}, {
+      session: [{ id: "session-a" } as Session],
+      question: { "session-a": [question] },
+      message: {
+        "session-a": [{ id: "msg-1", sessionID: "session-a", role: "assistant", time: { created: 1 } } as Message],
+      },
+      part: {
+        "msg-1": [{
+          id: "prt-1",
+          messageID: "msg-1",
+          sessionID: "session-a",
+          type: "tool",
+          tool: "question",
+          state: { status: "running" },
+        } as Part],
+      },
+    })
+    const childStores = createChildStores([["/test/project", store]])
+
+    const { setActionRefs, rejectQuestion } = await import("./session-actions")
+    setActionRefs(mockSdk as unknown as OpencodeClient, childStores, () => "/test/project", enqueueMaterialization)
+
+    // Success: no recovery enqueued — the normal question.rejected event flow clears state.
+    await rejectQuestion("session-a", "q-1")
+    expect(materializationCalls).toEqual([])
+
+    // Not-found: the request is stale server-side; the tail must be reconciled.
+    questionRejectError = Object.assign(new Error("question.reject failed (404): QuestionNotFoundError"), { status: 404 })
+    const stale = buildQuestion("q-stale", "session-a")
+    store.setState({ question: { "session-a": [stale] } })
+
+    let thrown: unknown
+    try {
+      await rejectQuestion("session-a", "q-stale")
+    } catch (error) {
+      thrown = error
+    }
+
+    expect(thrown).toBeInstanceOf(Error)
+    expect(store.getState().question["session-a"]).toBe(undefined)
+    expect(materializationCalls).toEqual([{ directory: "/test/project", sessionID: "session-a", messageID: "msg-1" }])
+  })
+})
+
 function buildQuestion(id: string, sessionId: string): QuestionRequest {
   return {
     id,
diff --git a/packages/ui/src/sync/session-actions.ts b/packages/ui/src/sync/session-actions.ts
index 1b695891..aa8cdb10 100644
--- a/packages/ui/src/sync/session-actions.ts
+++ b/packages/ui/src/sync/session-actions.ts
@@ -30,6 +30,8 @@ import { getImperativeSessionMessageLoader } from "./session-message-loader"
 import { cleanupPersistedSessionState } from "./session-deletion-cleanup"
 import { getRuntimeKey } from "@/lib/runtime-switch"
 import { isAmbiguousTransportFailure } from "@/lib/relay/transport-error"
+import { getStaleRunningToolMessageID } from "./materialization"
+import { normalizePath } from "@/lib/pathNormalization"
 
 const MESSAGE_REFETCH_LIMIT = 100
 const SEND_CONFIRMATION_REFETCH_LIMIT = 30
@@ -52,6 +54,10 @@ const UNREVERT_REFETCH_RETRY_MS = 150
 let _sdk: OpencodeClient | null = null
 let _childStores: ChildStoreManager | null = null
 let _getDirectory: () => string = () => ""
+// Optional ref into the sync layer's session-tail materialization queue. Used
+// to reconcile a trailing running tool part after a blocking request is
+// confirmed stale server-side (see recoverStaleBlockingRequest).
+let _enqueueSessionMaterialization: ((directory: string, sessionID: string, messageID: string) => void) | null = null
 type OptimisticAddInput = { sessionID: string; directory?: string | null; message: Message; parts: Part[] }
 type OptimisticRemoveInput = { sessionID: string; directory?: string | null; messageID: string }
 type OptimisticConfirmInput = OptimisticRemoveInput
@@ -139,10 +145,12 @@ export function setActionRefs(
   sdk: OpencodeClient,
   childStores: ChildStoreManager,
   getDirectory: () => string,
+  enqueueSessionMaterialization?: (directory: string, sessionID: string, messageID: string) => void,
 ) {
   _sdk = sdk
   _childStores = childStores
   _getDirectory = getDirectory
+  _enqueueSessionMaterialization = enqueueSessionMaterialization ?? null
 }
 
 export function setOptimisticRefs(
@@ -480,6 +488,29 @@ function restoreFilePartsToInput(fileParts: Array<Record<string, unknown>>): voi
   }
 }
 
+/**
+ * Server-confirmed directory that owns a session, from the session record
+ * (`directory`, then `project.worktree`). Mirrors the authoritative source in
+ * session-directory-resolution: holding a session in a child store proves
+ * containment, not ownership — a project's session list legitimately includes
+ * the sessions of its worktrees so the sidebar can group them — so reading
+ * ownership from the containing store reports the parent for a session that
+ * lives in a worktree, and every fetch is then addressed to a directory that
+ * does not own it.
+ */
+function resolveSessionOwnedDirectory(session: Session): string | null {
+  const record = session as Session & {
+    directory?: string | null
+    project?: { worktree?: string | null } | null
+  }
+  const raw = typeof record.directory === "string" && record.directory.trim().length > 0
+    ? record.directory
+    : typeof record.project?.worktree === "string" && record.project.worktree.trim().length > 0
+      ? record.project.worktree
+      : null
+  return raw ? normalizePath(raw) : null
+}
+
 function resolveDirectoryForBlockingRequest(
   type: "permission" | "question",
   sessionId: string,
@@ -493,10 +524,28 @@ function resolveDirectoryForBlockingRequest(
   for (const [directory, store] of stores.children) {
     const state = store.getState()
     const requestMap = type === "permission" ? state.permission : state.question
-    for (const requests of Object.values(requestMap) as Array<Array<{ id: string }> | undefined>) {
-      if (requests?.some((request) => request.id === requestId)) {
-        return directory
-      }
+    for (const requests of Object.values(requestMap) as Array<Array<{ id: string; sessionID?: string }> | undefined>) {
+      const request = requests?.find((candidate) => candidate.id === requestId)
+      if (!request) continue
+
+      // Ownership beats containment. The request belongs to one specific
+      // session, and the reply must reach the instance that actually tracks
+      // it — the directory the session record's server-confirmed `directory`
+      // names. The containing store's key only proves containment: a project
+      // store holds its worktree sessions too, and a reply addressed to the
+      // parent instance makes the server answer QuestionNotFoundError while
+      // the question stays pending in the worktree instance, leaving the
+      // session stuck on the running question tool. Fall back to the store
+      // key only when the session record carries no directory.
+      const requestSessionID = typeof request.sessionID === "string" && request.sessionID.length > 0
+        ? request.sessionID
+        : sessionId
+      const sessionRecord = requestSessionID
+        ? state.session.find((s) => s.id === requestSessionID)
+        : undefined
+      const ownedDirectory = sessionRecord ? resolveSessionOwnedDirectory(sessionRecord) : null
+      if (ownedDirectory) return ownedDirectory
+      return directory
     }
   }
 
@@ -537,6 +586,38 @@ export function isQuestionRequestNotFoundError(error: unknown): boolean {
   return /Question(?:\.)?NotFoundError|Question request not found/i.test(message)
 }
 
+/**
+ * Reconcile the trailing assistant tool part after a blocking request turned
+ * out to be stale server-side (reply/reject answered with not-found). The
+ * local request is removed (the server no longer tracks it), but the
+ * question/permission tool part can remain `running` with the session busy —
+ * the UI would stay on "asking question" with no recovery until the user
+ * stops the run. Enqueue the sync layer's settled-running-tool tail
+ * materialization so the part converges to the server's actual state.
+ */
+function recoverStaleBlockingRequest(sessionId: string): void {
+  const stores = _childStores
+  const enqueue = _enqueueSessionMaterialization
+  if (!stores || !enqueue || !sessionId) return
+
+  for (const [directory, store] of stores.children) {
+    const state = store.getState()
+    if (
+      !state.session.some((session) => session.id === sessionId)
+      && !Object.prototype.hasOwnProperty.call(state.message, sessionId)
+      && !Object.prototype.hasOwnProperty.call(state.session_status ?? {}, sessionId)
+      && !Object.prototype.hasOwnProperty.call(state.question ?? {}, sessionId)
+    ) {
+      continue
+    }
+    const messageID = getStaleRunningToolMessageID(state, sessionId)
+    if (messageID) {
+      enqueue(directory, sessionId, messageID)
+    }
+    return
+  }
+}
+
 function removeQuestionRequestFromChildStores(sessionId: string, requestId: string): boolean {
   const stores = _childStores
   if (!stores || !requestId) return false
@@ -1581,6 +1662,7 @@ export async function respondToQuestion(
   } catch (error) {
     if (isQuestionRequestNotFoundError(error)) {
       removeQuestionRequestFromChildStores(sessionId, requestId)
+      recoverStaleBlockingRequest(sessionId)
     }
     throw error
   }
@@ -1605,6 +1687,7 @@ export async function rejectQuestion(
   } catch (error) {
     if (isQuestionRequestNotFoundError(error)) {
       removeQuestionRequestFromChildStores(sessionId, requestId)
+      recoverStaleBlockingRequest(sessionId)
     }
     throw error
   }
diff --git a/packages/ui/src/sync/sync-context.tsx b/packages/ui/src/sync/sync-context.tsx
index 846e6fcc..91f027a1 100644
--- a/packages/ui/src/sync/sync-context.tsx
+++ b/packages/ui/src/sync/sync-context.tsx
@@ -2360,6 +2360,12 @@ export function SyncProvider(props: {
       props.sdk,
       childStores,
       () => opencodeClient.getDirectory() || props.directory,
+      (directory, sessionID, messageID) => {
+        enqueueSessionMaterialization(directory, sessionID, childStores, {
+          reason: "settled-running-tool",
+          messageID,
+        })
+      },
     )
     return () => {
       if (getImperativeSessionMessageLoader() === messageLoader) {