diff --git a/packages/tui/src/context/sync.tsx b/packages/tui/src/context/sync.tsx
index d0511c5183e4..a87e807f2c57 100644
--- a/packages/tui/src/context/sync.tsx
+++ b/packages/tui/src/context/sync.tsx
@@ -167,6 +167,71 @@ export const {
         .then((x) => (x.data ?? []).toSorted((a, b) => a.id.localeCompare(b.id)))
     }
 
+    // Insert a pending request into its per-session list, kept sorted by id so the
+    // binary `search` stays valid. Idempotent: skip a request a live `*.asked` event
+    // already added, so hydration and live events can interleave safely.
+    function upsertPermission(request: PermissionRequest) {
+      const requests = store.permission[request.sessionID]
+      if (!requests) {
+        setStore("permission", request.sessionID, [request])
+        return
+      }
+      const match = search(requests, request.id, (r) => r.id)
+      if (match.found) return
+      setStore(
+        "permission",
+        request.sessionID,
+        produce((draft) => {
+          draft.splice(match.index, 0, request)
+        }),
+      )
+    }
+
+    function upsertQuestion(request: QuestionRequest) {
+      const requests = store.question[request.sessionID]
+      if (!requests) {
+        setStore("question", request.sessionID, [request])
+        return
+      }
+      const match = search(requests, request.id, (r) => r.id)
+      if (match.found) return
+      setStore(
+        "question",
+        request.sessionID,
+        produce((draft) => {
+          draft.splice(match.index, 0, request)
+        }),
+      )
+    }
+
+    // Fetch pending prompts on (re)connect. The `*.asked` events fire once, at ask
+    // time, and aren't replayed, so a client that connects afterwards (e.g. after
+    // detaching the TUI) never sees them via events alone and would leave the agent
+    // blocked with no prompt to answer.
+    function hydratePending(workspace: string | undefined) {
+      const permissions = sdk.client.permission
+        .list({ workspace })
+        .then((x) => {
+          for (const request of x.data ?? []) {
+            if (permission.mode === "auto") {
+              void sdk.client.permission.reply({ requestID: request.id, reply: "once", workspace })
+              continue
+            }
+            upsertPermission(request)
+          }
+        })
+        .catch(() => {})
+      const questions = sdk.client.question
+        .list({ workspace })
+        .then((x) => {
+          for (const request of x.data ?? []) {
+            upsertQuestion(request)
+          }
+        })
+        .catch(() => {})
+      return Promise.all([permissions, questions])
+    }
+
     event.subscribe((event, { directory, workspace }) => {
       switch (event.type) {
         case "server.instance.disposed":
@@ -526,6 +591,7 @@ export const {
             }),
             sdk.client.provider.auth({ workspace }).then((x) => setStore("provider_auth", reconcile(x.data ?? {}))),
             sdk.client.vcs.get({ workspace }).then((x) => setStore("vcs", reconcile(x.data))),
+            hydratePending(workspace),
             project.workspace.sync(),
           ]).then(() => {
             setStore("status", "complete")
diff --git a/packages/tui/test/cli/cmd/tui/sync-live-hydration.test.tsx b/packages/tui/test/cli/cmd/tui/sync-live-hydration.test.tsx
index 398c5c9ab524..f27e349709ce 100644
--- a/packages/tui/test/cli/cmd/tui/sync-live-hydration.test.tsx
+++ b/packages/tui/test/cli/cmd/tui/sync-live-hydration.test.tsx
@@ -260,3 +260,38 @@ test("a message removed during hydration does not regain stale parts", async ()
     app.renderer.destroy()
   }
 })
+
+test("pending permissions and questions are hydrated on connect without a live event", async () => {
+  await using tmp = await tmpdir()
+  await Bun.write(`${tmp.path}/kv.json`, "{}")
+
+  const permission = {
+    id: "per_hydrated",
+    sessionID,
+    permission: "bash",
+    patterns: ["rm -rf /"],
+    metadata: {},
+    always: ["rm -rf /"],
+  }
+  const question = {
+    id: "que_hydrated",
+    sessionID,
+    questions: [{ question: "Proceed?", header: "Confirm", options: [{ label: "Yes", description: "do it" }] }],
+  }
+
+  // The TUI has just (re)attached: the *.asked events fired while it was
+  // detached, so the only way it can learn about these pending prompts is by
+  // fetching them on connect. No live event is emitted in this test.
+  const { app, sync } = await mount((url) => {
+    if (url.pathname === "/permission") return json([permission])
+    if (url.pathname === "/question") return json([question])
+    return undefined
+  }, tmp.path)
+
+  try {
+    expect(sync.data.permission[sessionID]).toEqual([permission])
+    expect(sync.data.question[sessionID]).toEqual([question])
+  } finally {
+    app.renderer.destroy()
+  }
+})
diff --git a/packages/tui/test/fixture/tui-sdk.ts b/packages/tui/test/fixture/tui-sdk.ts
index d1cf3c7dfc2a..27bdc40467a8 100644
--- a/packages/tui/test/fixture/tui-sdk.ts
+++ b/packages/tui/test/fixture/tui-sdk.ts
@@ -102,6 +102,7 @@ export function createFetch(override?: FetchHandler, events?: ReturnType<typeof
       return json({ location: { directory, project: { id: "proj_test", directory } }, data: [] })
     if (url.pathname === "/provider") return json({ all: [], default: {}, connected: [] })
     if (url.pathname === "/session") return json([])
+    if (url.pathname === "/permission" || url.pathname === "/question") return json([])
     if (url.pathname === "/vcs") return json({ branch: "main" })
     throw new Error(`unexpected request: ${url.pathname}`)
   }) as typeof globalThis.fetch