Cowork installation causes Windows 11 boot failure requiring System Restore

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?

After enabling Cowork and completing the VM download, Claude prompts a restart. After restarting, Windows fails to boot and enters Automatic Repair mode. This happened twice in a row, requiring a full System Restore both times to recover.

What Should Happen?

Windows should boot normally after Cowork installation and restart.

Error Messages/Logs

Windows Automatic Repair screen on boot. No other error messages visible.

Steps to Reproduce

1. Fresh install of Claude Desktop from claude.ai/download
2. Open Cowork tab and click Enable
3. Wait for VM download to complete (~95%)
4. Restart when prompted by Claude
5. Windows fails to boot — Automatic Repair screen appears

Claude Model

None

Is this a regression?

No, this never worked

Last Working Version

_No response_

Claude Code Version

Claude Desktop latest (downloaded from claude.ai/download)

Platform

Anthropic API

Operating System

Windows

Terminal/Shell

PowerShell

Additional Information

System Restore was required twice to recover. Cowork VM installation appears to interfere with Windows boot process.