[BUG] Manual /compact errors out - so I have to saturate context to 100% so autocompact could run

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 I manually try to run /compact it errors out, so I have to saturate my context to 100% because auto-compact always seems to work.

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

What Should Happen?

Manual command '/compact' should run successfully same as the 'auto-compact'

Error Messages/Logs

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

Steps to Reproduce

When you get to 60% or 70% of context utilisation, try to run /compact manually.

Claude Model

Sonnet (default)

Is this a regression?

I don't know

Last Working Version

_No response_

Claude Code Version

2.0.14 (Claude Code)

Platform

Anthropic API

Operating System

macOS

Terminal/Shell

Terminal.app (macOS)

Additional Information

_No response_