[BUG] Cowork: AskUserQuestion picker never renders if user switches chats during pending call — questions permanently marked "Failed" after app restart (macOS)

Preflight Checklist

• [x] I have searched existing issues and this hasn't been reported yet
• [x] This is a single bug report (please file separate reports for different bugs)
• [x] I am using the latest version of Claude Code

What's Wrong?

In Cowork mode, when a task calls AskUserQuestion and the user has navigated away from that chat before the question renders, the picker UI never mounts on return. The chat shows only the "Using AskUserQuestion…" tool-running indicator. The state is unrecoverable: typing in the input box does nothing, and only a full app restart unfreezes the UI — at which point the questions appear in chat history but are each marked "Failed", with no way to answer them.

Net effect: any task that uses AskUserQuestion becomes permanently unanswerable the moment the user does what Cowork is designed for — start a task and switch away. The task has to be retried from scratch.

What Should Happen?

When returning to a Cowork chat with a pending AskUserQuestion call, the picker should be visible and answerable, regardless of whether the chat was the foreground view at the moment the tool fired.

Error Messages/Logs

Steps to Reproduce

1. Start a Cowork task that will call AskUserQuestion (any skill with a clarification step, a plan-mode confirmation flow, or just ask Claude to ask you something before continuing).
2. Switch to another Cowork chat before the question fires.
3. A desktop notification arrives saying input is needed.
4. Click back into the original chat. Observe: only "Using AskUserQuestion… [n]s" is visible. No question card, no options, no input.
5. The UI stays frozen on the indicator. Typing in the input box does not recover it.
6. Quit and relaunch Claude Desktop (Cmd+Q + reopen).
7. Observe: the questions finally render in chat history, but each option is marked "Failed." The tool call has resolved with no input during the dead-render window; the questions can no longer be answered.

Claude Model

Opus

Is this a regression?

I don't know

Last Working Version

_No response_

Claude Code Version

Claude 1.8555.2 (a476c3) 2026-05-22T23:04:37.000Z

Platform

Anthropic API

Operating System

macOS

Terminal/Shell

Other

Additional Information

This appears to be a specific failure mode of the broader "Cowork renderer coupled to active focus" pattern, but with worse impact than the general case because pending AskUserQuestion calls don't just fail to render — they resolve as Failed and become irrecoverable.
Closed precedent issues describing the same root cause without the AskUserQuestion variant:

#44776 (closed as duplicate) — task responses vanish after switching between tasks
#44686 (closed as inactive)
#26921 (closed) — Cowork UI freezes mid-response, other threads blank until app restart, names the exact "until app restart" symptom
#26805 (closed) — responses not rendering until user types; oncall-labelled
#40142 — Cowork Dispatch responses never render, TypeError in renderer

Related closed AskUserQuestion render issues:

#26940 — AskUserQuestion widget doesn't render in Cowork/LAM sessions, spinner hangs indefinitely (lam_tool_permission_stalled log evidence)
#29530, #29547, #29733, #29773, #33564 — assorted AskUserQuestion-returns-empty / picker-never-renders reports

The workaround from #26921 ("send any message to force re-render") does not apply here because by the time the user is back in the chat, the picker is no longer in conversation state — only the indicator remains. The OP workaround from #26940 ("re-prompt with explicit enough instructions that the skill doesn't need to ask") is the only practical mitigation, but requires the user to predict in advance which prompts will trigger an AskUserQuestion call.

<img width="825" height="344" alt="Image" src="https://github.com/user-attachments/assets/21409e3d-b636-4ebb-a73e-371dd8bccc11" />

<img width="763" height="365" alt="Image" src="https://github.com/user-attachments/assets/1d8fc9ba-9090-4217-883d-f67ca46685d4" />