[BUG] Quick Entry sends message on new chats but silently fails on existing chats

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?

Quick Entry (triggered by double-Option) works correctly for new chats but silently fails when continuing existing chats.

When using Quick Entry to send a message to an existing conversation:

1. Double-tap Option to open Quick Entry
2. 2. Take a screenshot or type a message
3. 3. Press Enter to send
4. 4. Quick Entry closes and the main Claude Desktop window opens, but the message is never sent to the conversation

This happens every time on existing chats. New chats work fine.

Troubleshooting already attempted:

• Restarted computer
• - Updated Claude Desktop to latest version
• - - Force quit and relaunched the app
• - - - Verified Screen Recording and Accessibility permissions are enabled
• - - - - Cleared ~/Library/Application Support/Claude/Cache ("nuclear option")

After clearing the cache, Quick Entry started working on new chats but still fails on existing chats being continued.

What Should Happen?

Quick Entry should send the message to the existing conversation that was selected, just like it does for new chats. The message and any attached screenshots should appear in the conversation after pressing Enter.

Error Messages/Logs

No error messages. The failure is silent — Quick Entry closes and the main window opens, but no message is sent.

Steps to Reproduce

1. Open Claude Desktop and start a conversation (send at least one message so it becomes an "existing" chat)
2. 2. Navigate away or minimize Claude Desktop
3. 3. Double-tap Option to open Quick Entry
4. 4. Type a message or take a screenshot
5. 5. Press Enter to send
6. 6. Observe: Quick Entry closes, main Claude Desktop window opens, but the message is NOT sent to the conversation

Note: This only happens with existing/continuing chats. If you use Quick Entry to start a brand new chat, it works correctly.

Claude Model

None

Is this a regression?

Yes, this worked in a previous version

Last Working Version

_No response_

Claude Code Version

2.1.85 (Claude Code) — but this bug is in the Claude Desktop app, not Claude Code CLI

Platform

Anthropic API

Operating System

macOS

Terminal/Shell

Terminal.app (macOS)

Additional Information

This bug is specifically in the Claude Desktop macOS app's Quick Entry feature, not in Claude Code CLI.

macOS version: Sequoia 15.4

The issue appears to be in how Quick Entry resolves which conversation to route the message to. New conversations route correctly, but existing conversations don't receive the dispatched message. The Quick Entry UI itself works fine (opens, accepts input, closes on Enter) — it's the message delivery to existing chats that silently fails.