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

Preflight Checklist

What’s Wrong?

Auto-compact doesn’t work. Anthropic flagged this as fixed on January 15, but the issue persists. When context window fills up, instead of auto-compacting and continuing the conversation, one of two things happens:

1. Messages get bounced back to the input box with no error (most common).
2. Occasionally, a “limit reached” error appears.

This happens even when the context being fed the chat shouldn’t be anywhere near the 200k token limit.

What Should Happen?

Auto-compact should trigger automatically when approaching context limits, allowing the conversation to continue without manual intervention.

Error Messages/Logs

Usually none; message just silently returns to input box.
Occasionally "limit reached" error.

Steps to Reproduce

1. Create a new chat within a Claude.ai project (mine is ~3% capacity).
2. Feed it a substantial amount of context (documents, instructions, etc.).
3. Continue chatting until context builds up.
4. Attempt to send another message.
5. Message gets returned to input box OR “limit reached” error appears.
6. Auto-compact never triggers.

Claude Model

Not sure / Multiple models

Is this a regression?

Yes, this worked in a previous version

Last Working Version

Claude.ai (web/desktop) worked prior to January 14 major outage and January 15 compaction incident. Broken since.

Claude Code Version

N/A

Platform

Other

Operating System

Windows

Terminal/Shell

Other

Additional Information

Issue was reported previously and marked as resolved January 15. Still broken as of January 17.
Happens within Projects, unsure if it affects non-Project chats.

Note: Submitting here because there’s no dedicated bug tracker for Claude.ai. This affects the web and desktop interfaces, not Claude Code specifically. Auto-compact was functional before the January 14 outage and has remained broken despite being flagged as fixed on January 15.