[BUG] Claude not compacting

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?

When pasting in images noticing claude not auto compacting and hitting it's 20MB limit. Only after compacting manually will claude continue

MacOS
Claude Code 2.1.89

What Should Happen?

Claude should see it's reaching its context limit and auto compact.

Error Messages/Logs

Steps to Reproduce

Use claude for a time running long conversations with multiple image processing.

Claude Model

None

Is this a regression?

Yes, this worked in a previous version

Last Working Version

_No response_

Claude Code Version

2.1.89

Platform

Anthropic API

Operating System

macOS

Terminal/Shell

Terminal.app (macOS)

Additional Information

_No response_