Preflight Checklist I have searched existing issues and this hasn't been reported yet This is a single bug report (please file separate reports for different bugs) I am using the latest version of Claude Code What's Wrong? Auto-compact d...

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Auto-compact functionality in Claude.ai (web and desktop) has been broken since January 14, 2026, despite being marked as fixed on January 15. When the context window fills up, messages either bounce back to the input box silently or show a "limit reached" error instead of automatically compacting and continuing the conversation. Multiple paying subscribers report this regression affects long-form work, with some experiencing the issue across all platforms (browser, desktop, mobile). The problem persists as of January 23, with users frustrated by lack of public acknowledgment from Anthropic despite private confirmation they're investigating.

[BUG] Auto-compact not triggering on Claude.ai (web & desktop) despite being marked as fixed · Issue #18866 · anthropics/claude-code