[BUG] Cowork Sessions - Timing Out with API Error

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?

Cannot get sessions to complete in Cowork. Few simple sessions are able to run very slowly on sonnet, but not larger models.

What Should Happen?

Cowork should be able to run and complete the sessions in a timely manor.

Error Messages/Logs

API Error: The operation timed out.

Steps to Reproduce

1. Navigate to Cowork
2. Create a session
3. Wait for it to time out
4. Certain projects are worse than others

Claude Model

Opus

Is this a regression?

Yes, this worked in a previous version

Last Working Version

The last time it worked as its supposed to was pushing 2 weeks ago.

Claude Code Version

Claude 1.6608.0 (f65729) 2026-05-07T14:16:09.000Z

Platform

Anthropic API

Operating System

Windows

Terminal/Shell

Windows Terminal

Additional Information

<img width="1910" height="1332" alt="Image" src="https://github.com/user-attachments/assets/69909b1d-affe-4895-8ac8-696cf9afb6cd" />