Saturday, January 24, 2026

[BUG]: Auto-Compact Fails to Trigger on Claude.ai (Web & Desktop) Despite Marked Fix – Issue #18866 · anthropics/claude-code · GitHub

Navigating the Challenges of Auto-Compaction in Claude.ai: A Preflight Checklist

The auto-compaction feature in Claude.ai has faced significant functionality issues since January 14. Despite being flagged as resolved on January 15, users continue to experience disruptive errors.

Key Observations:

  • What’s Going Wrong?

    • Messages often bounce back with no clear error.
    • Intermittent “limit reached” errors occur, even well below the 200k token limit.
  • Expected Functionality:

    • Auto-compaction should trigger automatically when context limits are approached, facilitating uninterrupted conversation.

Steps to Experience the Issue:

  1. Start a new chat within a Claude.ai project.
  2. Input substantial context.
  3. Monitor the performance when the message limit is reached.

This regression highlights a critical gap in user experience, impacting both web and desktop interfaces.

🔗 Engage with this summary if you’ve faced similar challenges! Let’s collaborate on finding solutions. Share your experiences below!

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