[BUG] Context compression in long sessions drops earlier conversation details

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?

Context compression in long sessions drops earlier conversation details, which makes multi-step feature work painful. Claude irrecoverably "forgets" what we were working on mid-session. This is severely problematic when working on complex tasks.

What Should Happen?

Claude shouldn't forget what we're working on mid-session! If compression is required, surely it could save whatever we were working on in a file, and then load that file when compression is complete.

Error Messages/Logs

Steps to Reproduce

Just troubleshoot an issue long enough and this will happen. At least in the Claude app, you don't even know this has happened until Claude suddenly acts like it doesn't know what you're talking about.

Claude Model

None

Is this a regression?

Yes, this worked in a previous version

Last Working Version

_No response_

Claude Code Version

Claude Code version 2.1.56, running Claude Opus 4.6 (claude-opus-4-6)

Platform

Anthropic API

Operating System

macOS

Terminal/Shell

Other

Additional Information

_No response_