[Bug] Compact Fails When Context Window Nearly Full, Requires Restart

Resolved 💬 10 comments Opened Sep 16, 2025 by oborchers Closed Nov 3, 2025

Bug Description
Compact does not work properly for a couple of days now. When I am at 5% of remaining context window left and I run /compact I get an error that it failed because the conversation is too long. Howver: If I then exit the conversation and run claude --continue + /compact it works on the second try.

Environment Info

  • Platform: darwin
  • Terminal: iTerm.app
  • Version: 1.0.115
  • Feedback ID: 4ac0357e-962c-4ccd-90af-5ee34469b677

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