[BUG] Claude CoWork 1M context error on a Max plan

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?

I am constantly seeing the 1M context error in my cowork chats even though I haven't hit my usage limits. The only workaround for me is to start a new conversation but then I am giving all the context again. The auto compact of conversation doesn't trigger anymore and I cannot manually trigger one either in Claude Cowork.

<img width="589" height="253" alt="Image" src="https://github.com/user-attachments/assets/cc4e7706-1eb7-49b9-b3b0-fd9f3e74dfea" />
<img width="983" height="739" alt="Image" src="https://github.com/user-attachments/assets/a885366f-44a0-42c8-90ea-0c3d4d23a377" />

What Should Happen?

The extra usage credits shouldn't be used when Max usage limits have not been hit

Error Messages/Logs

Steps to Reproduce

Start a new conversation with Opus (high) and after couple or more conversations, you will hit the 1M context error.

Claude Model

None

Is this a regression?

Yes, this worked in a previous version

Last Working Version

_No response_

Claude Code Version

Claude 1.11187.1 (370d3b) 2026-06-04T17:30:35.000Z

Platform

Anthropic API

Operating System

macOS

Terminal/Shell

Terminal.app (macOS)

Additional Information

_No response_