[BUG] Error: Error during compaction: Error: Conversation too long.

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 have had several times now that I ran out of context while auto-compact was on and it told me to type
/compact to fix it only for that to say after I typed /compact: ⎿  Error: Error during compaction: Error: Conversation too long. Press esc twice to go up a few messages and try again

The fix is to type /clear - but this deletes all context for the next command.

What Should Happen?

Auto-compact should fire off before it gets to the point that it doesn't have enough context left to auto-compact.

Error Messages/Logs

Error: Error during compaction: Error: Conversation too long. Press esc twice to go up a few messages and try again

Steps to Reproduce

Reproduction is not easy - it happens irregularly.

Claude Model

Opus

Is this a regression?

Yes, this worked in a previous version

Last Working Version

_No response_

Claude Code Version

 2.0.69 (Claude Code)

Platform

Anthropic API

Operating System

Windows

Terminal/Shell

PowerShell

Additional Information

_No response_