[BUG] Cowork hang at startup

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?

Environment

• Device: M1 Mac Mini (headless, accessed via Tailscale)
• macOS: [your version]
• Claude Desktop: latest
• Claude Code CLI: 2.1.119

What happened
Cowork sessions hang at "starting up" and never complete.
All sessions show cliSessionId: none in main.log.
After clearing sessions and signing back in, app shows "legacy model."
Claude Code CLI works fine independently. launchd jobs unaffected.

What I tried

• Updated CLI from 2.1.29 to 2.1.119
• Cleared claude-code-vm cache
• Cleared local-agent-mode-sessions
• Unlocked macOS keychain
• Full reboot
• Sign out / sign back in

Logs
[Attach cowork_vm_node.log and main.log from ~/Library/Logs/Claude/]

What Should Happen?

Claude Cowork should run the scheduled tasks and respond to keyboard input.

Error Messages/Logs

**Environment**
- Device: M1 Mac Mini (headless, accessed via Tailscale)
- macOS: [your version]
- Claude Desktop: latest
- Claude Code CLI: 2.1.119

**What happened**
Cowork sessions hang at "starting up" and never complete. 
All sessions show cliSessionId: none in main.log. 
After clearing sessions and signing back in, app shows "legacy model."
Claude Code CLI works fine independently. launchd jobs unaffected.

**What I tried**
- Updated CLI from 2.1.29 to 2.1.119
- Cleared claude-code-vm cache
- Cleared local-agent-mode-sessions
- Unlocked macOS keychain
- Full reboot
- Sign out / sign back in

**Logs**
[Attach cowork_vm_node.log and main.log from ~/Library/Logs/Claude/]

Steps to Reproduce

Simply prompting causes cowork to not work No other information available. Unable to stop cowork chat. Have to hard stop app and reboot M1 Mac Mini

Claude Model

Sonnet (default)

Is this a regression?

Yes, this worked in a previous version

Last Working Version

_No response_

Claude Code Version

2.1.119

Platform

Other

Operating System

macOS

Terminal/Shell

Terminal.app (macOS)

Additional Information

_No response_