diff --git a/src/servers/sidecar/claude/claude-manager.ts b/src/servers/sidecar/claude/claude-manager.ts
index 38a170b7..49f5b5e7 100644
--- a/src/servers/sidecar/claude/claude-manager.ts
+++ b/src/servers/sidecar/claude/claude-manager.ts
@@ -463,6 +463,30 @@ function armStall(session: PersistentSession): void {
     session.stallTimer = undefined;
     return;
   }
+
+  // ── A turn WAITING ON A PERSON is not a stalled turn ──
+  //
+  // Parking on `AskUserQuestion` or a plan gate means emitting nothing until somebody answers — that is
+  // what parking is. This timer could not tell that from a wedged turn, and at 10 minutes against gates
+  // that wait 20, it always won:
+  //
+  //   10m  the turn is declared dead, `isGenerating` goes false, and the session is torn down
+  //   20m  the gate's own timeout would have resolved it truthfully — never reached
+  //
+  // The card stays on screen with nothing behind it, and clicking an answer does nothing, because an
+  // answer's only receipt is the `tool:result` that the gate emits when it unblocks — and the gate is
+  // gone. Reported as "the chat becomes unusable, I have to refresh and send another message", which is
+  // exactly what it would look like from the outside.
+  //
+  // So a session with an outstanding question or plan is left alone here. It is not unbounded: each gate
+  // holds its own 20-minute timer and resolves with a sentence written for the agent, after which the
+  // turn speaks again and this re-arms on the next event.
+  const waitingOnAPerson = session.pendingQuestions.size > 0 || session.pendingPlans.size > 0;
+  if (waitingOnAPerson) {
+    session.stallTimer = undefined;
+    return;
+  }
+
   const compacting = session.compactStartedAt !== undefined;
   session.stallTimer = setTimeout(
     () => {
@@ -1030,6 +1054,9 @@ async function questionGate(session: PersistentSession, toolCallId: string): Pro
   return new Promise<string>((resolve) => {
     const timer = setTimeout(() => {
       session.pendingQuestions.delete(toolCallId);
+      // Re-arm: the turn is about to speak again, and from here a silence IS a stall. `armStall` skips
+      // itself while any gate is still outstanding, so a second unanswered question keeps the reprieve.
+      armStall(session);
       console.warn(`[claude:question:${session.sessionKey}] no answer in 20m`);
       resolve(
         'The user has not answered yet — they may be away from the screen. The question is still on theirs, ' +
@@ -1067,6 +1094,9 @@ export function answerClaudeQuestion(sessionKey: string, userId: number, toolCal
   if (!session || !pending) return false;
   clearTimeout(pending.timer);
   session.pendingQuestions.delete(toolCallId);
+  // The turn resumes now, so silence stops being legitimate and the watchdog goes back on. `armStall`
+  // skips itself while another gate is outstanding, so answering one of two questions keeps the reprieve.
+  armStall(session);
   pending.resolve(answer);
   return true;
 }
diff --git a/src/servers/sidecar/claude/stall-parked.test.ts b/src/servers/sidecar/claude/stall-parked.test.ts
new file mode 100644
index 00000000..9c4ecab6
--- /dev/null
+++ b/src/servers/sidecar/claude/stall-parked.test.ts
@@ -0,0 +1,24 @@
+import { describe, expect, test } from 'bun:test';
+
+// The rule the fix encodes, exercised as the predicate rather than through a live harness: a session
+// waiting on a person must not be treated as stalled.
+const stallApplies = (isGenerating: boolean, questions: number, plans: number) =>
+  isGenerating && questions === 0 && plans === 0;
+
+describe('stall watchdog vs a parked turn', () => {
+  test('a generating turn with nothing pending is watched', () => {
+    expect(stallApplies(true, 0, 0)).toBe(true);
+  });
+  test('a turn parked on a question is NOT stalled — it is waiting', () => {
+    expect(stallApplies(true, 1, 0)).toBe(false);
+  });
+  test('a turn parked on a plan decision is not either', () => {
+    expect(stallApplies(true, 0, 1)).toBe(false);
+  });
+  test('answering one of two questions keeps the reprieve', () => {
+    expect(stallApplies(true, 1, 0)).toBe(false);
+  });
+  test('a turn that is not generating is never stalled', () => {
+    expect(stallApplies(false, 0, 0)).toBe(false);
+  });
+});