/compact fails with 'Conversation too long' when context limit is reached

[Asses13]

Bug Description

/compact fails with an error when the conversation reaches the context limit — the exact situation where /compact is needed most. This creates a deadlock: the user cannot compact, cannot continue, and is forced to /clear (losing all context).

Steps to Reproduce

1. Use Claude Code in a long session until "Context limit reached · /compact or /clear to continue" appears
2. Run /compact
3. Observe the error

Error Messages

First attempt:

❯ /compact
Error: Error during compaction: Error: Conversation too long. Press esc twice to go up a few messages and try again.

Subsequent attempts — same error, then the session becomes completely unresponsive:

API Error: 400 {"type":"error","error":{"type":"invalid_request_error","message":"messages: text content blocks must contain non-whitespace text"},"request_id":"req_011CXnuVCF3KmwzeqdM4gFNZ"}

Expected Behavior

/compact should always succeed, especially when the context limit is reached. Possible approaches:

• Progressively drop older messages before attempting compaction
• Use a smaller/faster model for the compaction summary when context is too large
• Truncate the conversation to fit within limits before summarizing

Environment

• Claude Code version: 2.1.31
• OS: Ubuntu Linux 6.8.0-94-generic (x86_64)
• Model: claude-opus-4-5-20251101

Impact

High — This is a Catch-22: /compact is the recommended action when context is full, but it fails precisely in that situation. The only workaround is /clear, which destroys all session context including task progress. This happens consistently across sessions and projects.

Additional Context

The "Press esc twice to go up a few messages and try again" suggestion does not help — the error persists regardless. After the compaction failure, the session often enters a broken state where even normal messages fail with the text content blocks must contain non-whitespace text API error.

[github-actions]

Found 3 possible duplicate issues:

1. /compact fails with 'Conversation too long' error #22418
2. [BUG] /compact always fails with "Conversation too long" since v2.1.23 (regression) #21853
3. [BUG] Error: Error during compaction: Error: Conversation too long. Press esc twice to go up a few messages and try again. #22051

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🤖 Generated with Claude Code

[Whit3Wizard]

I can confirm this regression. My workflow has been processing book content (reading 10-20+ chapter files,
synthesizing notes) reliably for hundreds of books over the past weeks as I use it to take notes on ebooks I want to read.

This morning (Feb 4), the same workflow started hitting context limits and /compact fails to recover. I've tried:

• Multiple fresh sessions
• Restarting Claude Code
• Restarting my PC entirely

Same result each time - context fills up and /compact doesn't help, forcing /clear which loses all work progress.

Environment:

• Claude Code version: 2.1.31
• Platform: Linux (WSL2)
• Model: Opus 4.5

Workflow that broke:

• Reading 5-10 book chapter files sequentially
• Previously handled 10-20+ files per session with no issues
• No changes to my configuration of the slash command I created or CLAUDE.md

This started immediately after updating to recent versions. The timing aligns with the v2.1.30 session memory changes.

[FilipeAleixo]

Mine either fails because 'Conversation too long', or doesn't even do anything and just stays idle, always showing 0 tokens consumed.

In summary I can't even compact the conversation at all at this point, not even restarting CC like when the 'Conversation too long' issue appeared in the past. I have to always start a new session from scratch, honestly this sucks badly.

[OBugroviy]

Same issue

❯ /compact
⎿ Error: Error during compaction: Error: Conversation too long. Press esc twice to go up a few messages and try again.

model: Sonnet 1M context

[Hormold]

Additional severity report: In some cases this is worse than just /compact failing — the app becomes completely bricked.

When context limit is reached with a sufficiently large conversation (heavy CLAUDE.md + many skills + MCP servers):

1. All messages blocked: "Context limit reached"
2. /compact fails: "Conversation too long"
3. Rewind (Esc twice) fails: "Conversation too long"
4. /clear is also blocked — the context limit gate blocks ALL input, including recovery commands
5. No way to exit the screen — user must force-kill the terminal process

This is not just data loss from /clear — it's a complete app freeze requiring kill/Ctrl+C/close terminal.

Screenshot from my session showing the deadlock: #23809

Environment: macOS, latest Claude Code, large project with extensive CLAUDE.md, 30+ skills, and MCP servers.

[russ2370]

Experiencing the same issue — Claude Code in VS Code integrated terminal

Hitting this exact same compaction deadlock on Claude Code 2.1.32, running Opus 4.6 inside the VS Code integrated terminal on the batch-processor branch of a medical imaging application project.

❯ /compact
  ⎿  Error: Error during compaction: Error: Conversation too long. Press esc twice to go up a few
     messages and try again.

Environment:

• Claude Code: 2.1.32
• Model: Opus 4.6
• Context usage at time of failure: 74% (604,765 tokens)
• Context left until auto-compact: 11%
• Session: 16 files changed, +800 -303
• Platform: VS Code integrated terminal

The session becomes completely unrecoverable after this error. The "press esc twice" suggestion does nothing. Auto-compact also fails to trigger before the context reaches this broken state.

This is a critical workflow blocker — the tool is unusable for any non-trivial session that runs long enough to need compaction, which is exactly the scenario where it's needed most.