Both /compact command and auto-compaction broken - 'conversation too long' error

[caffeinebounce]

Description

Both manual /compact and automatic compaction are broken. The /compact command consistently fails with "Conversation too long. Press esc twice to go up a few messages and try again" even when there is available context remaining.

Additionally, auto-compaction is also not working - the system does not automatically compact when approaching token limits as expected.

Environment

• Claude Code version: Latest (as of 2025-01-14)
• OS: macOS (Darwin 25.2.0)
• Model: claude-opus-4-5-20251101

Steps to Reproduce

1. Start a Claude Code session
2. Have a conversation that uses some context
3. Run /compact - fails with "conversation too long" error
4. Continue conversation until approaching limits - auto-compaction does not trigger

Expected Behavior

• /compact should summarize and reduce context when there's available space
• Auto-compaction should trigger when approaching token limits

Actual Behavior

• /compact always fails with "conversation too long" regardless of actual usage
• Auto-compaction does not trigger

Related Issues

This appears related to previously reported issues:

• [Bug] Compact command fails with "Conversation too long" error despite sufficient context window available #10556
• BUG: /compact command always fails with 'Conversation too long' error #10299
• [Bug] Compact command fails with "Conversation too long" error #9799
• [Bug] Compact Command Fails with "Conversation Too Long" Error #9493

However, those issues focus on /compact - this report confirms auto-compaction is also broken, making the suggested workaround ineffective.

Impact

Without working compaction (manual or automatic), users must manually manage sessions by starting new ones, losing conversation continuity. This significantly impacts long-running sessions and complex multi-step tasks.

[dwight000]

The web version on claude.ai is acting up. Also see this error. I havent seen any compactions at all today. I also have seen another error (i dont have a screenshot) saying too many attachments.

"Your message will exceed the length limit for this chat. Try shortening your message or starting a new conversation."

[mihailmariusiondev]

Only happens in 2.1.7. If you rollback to 2.1.4 it works

[Wittyusername12]

Same issue with Claude AI on the web.

[aconcepcion]

Wtf are Anthropic doing? First they have a long system outage, and now they've vibe coded a fix that broke compacting. Super frustrating and incompetent approach, especially at the prices we're paying.

[vantzs]

Still having issues.. very frustrating considering I'm paying for 2x $200 a month accounts and they are both useless right now.

[aconcepcion]

Claude has been unusable basically for the past two days. First with the general global outage that took hours to resolve, and now with this. They should compensate with additional credits, etc., find some way to make it up to users, especially Max subscribers. This is just unacceptable.

[aepinformatica]

They opened an incident on Claude Status and seems they're releasing a patch

[dwight000]

Not sure if web is fixed or different issue. I dont get the error anymore on claude.ai, but it just does "nothing" now. If i turn off thinking i get further.

[aconcepcion]

I'm now having the exact same problem as @dwight000. I write a prompt, attach a few screenshots, and then I press enter. For a brief moment it looks like my prompt is getting processed, but then my prompt is just hanging there in the text box again, waiting to be sent. Nothing's happening, except I get a "conversation not found" red popup. This is just very odd. Claude has become a completely unusable product for the last three days. This is just crazy...

[vantzs]

I finally sent a ticket into ***@***.*** to see if I can get some resolution. I'm having similar issues. Claude will be in the middle of working on something, I'll step away for a minute or two and come back and all the steps, the chat, everything is just gone. My only solution has been telling Claude to create a transcript and update it after every step so he knows where to pick back up from.

…

On Thu, Jan 15, 2026 at 10:10 PM GaijinEagle ***@***.***> wrote: *aconcepcion* left a comment (anthropics/claude-code#18211) <#18211 (comment)> I'm now having the exact same problem as @dwight000 <https://github.com/dwight000>. I write a prompt, attach a few screenshots, and then I press enter. For a brief moment it looks like my prompt is getting processed, but then my prompt is just hanging there in the text box again, waiting to be sent. Nothing's happening. This is just very odd. Claude has become a completely unusable product for the last three days. This is just crazy... — Reply to this email directly, view it on GitHub <#18211 (comment)>, or unsubscribe <https://github.com/notifications/unsubscribe-auth/AB323OJQ6AKZFXUJHINBHVD4HBJA3AVCNFSM6AAAAACRW2XH2SVHI2DSMVQWIX3LMV43OSLTON2WKQ3PNVWWK3TUHMZTONJXHEYDIMBVGY> . You are receiving this because you commented.Message ID: ***@***.***>

-- Sincerely, Vantz M. Stockwell 704-931-8324

[elfieelfieelfie]

Confirming this is still reproducible and matches my experience.

After auto-compaction triggers once:

• subsequent prompts silently fail (revert to draft, no generation)
• occurs across web, desktop, and iOS
• also reproducible in brand-new conversations after their first compaction
• attachments worsen the failure (prompt never submits)

This looks like conversation-state corruption caused by the compaction pipeline, not a client issue.

I previously filed #18482, which appears to be a duplicate of this issue.

[solangerainha]

+1 for what @dwight000 reported.

I've been having the same issue since the compaction problem was flagged as "fixed". I send messages in claude.ai and they bounce back to the typing box. There's no error about limits reached or anything, but testing the same thing on the mobile app does return the limits error.

Disabling Thinking lets me keep sending messages but eventually it hits the problem too.