[BUG] /compact command fails at 0% context remaining

Preflight Checklist

• [x] I have searched existing issues and this hasn't been reported yet
• [x] This is a single bug report (please file separate reports for different bugs)
• [x] I am using the latest version of Claude Code

What's Wrong?

When the context window reaches 0% during a long conversation, running the /compact command throws an error instead of compressing the conversation. The conversation becomes completely stuck — no further interaction is possible, and the only
option is to run /clear, which loses all conversation context.

What Should Happen?

The /compact command should gracefully compress the conversation even when the context window is at 0%. Ideally, Claude Code
should also auto-compact before reaching 0% to prevent the conversation from becoming unrecoverable. At minimum, /compact
should never fail — it should always be able to summarize and free up context space.

Error Messages/Logs

● 예시 답안 섹션은 확인했습니다. 이건 프리뷰에서의 예시 답안 표시 부분입니다. 하지만 스크린샷의 ⓐ : 빈 줄은 **PDF 출력 시의     
                                                                                                                                  
    답안란(학생이 쓰는 칸)**입니다. 이 부분도 찾아봐야 합니다.                                                                    
                                                                                                                                  
         ● Searched for 1 pattern (ctrl+o to expand)                                                                              
                                                                                                                                  
                                                                                                                                  
                                                                                                                                  
  ❯ 이 스크린샷은 '지칭 추론' 유형에서 '동일/상이 의미 선별' 세부 유형인데, pdf 렌더링 결과물에서 각 알파벳 표기 뒤에 있는        
  순수                                                                                                                            
     영어 텍스트에만 밑줄이 쳐지면 돼. 지금은 '(A) those tiny ~~ sweat' 여기 통째로 쳐져있지만 those 부터 sweat 까지 부분만       
                                                                                                                                  
    쳐지게 바꿔줘.                                                                                                                
    ⎿  [Image #3]                                                                                                                 
           ⎿  Context limit reached · /compact or /clear to continue

Steps to Reproduce

1. Start a Claude Code session in a large project directory 2. Have a long conversation with many tool calls (file reads, edits, searches, etc.) until the context window indicator reaches

0%

1. Once context is at 0%, Claude shows "Context limit reached · /compact or /clear to continue"
2. Run /compact
3. The command fails with an error instead of compressing the conversation
4. The session is now stuck — neither /compact nor further prompts work
5. The only recovery option is /clear, which erases all conversation context

Environment: Windows 11, Claude Code CLI (latest version), using bash shell via MSYS2/Git Bash

Claude Model

Opus

Is this a regression?

No, this never worked

Last Working Version

_No response_

Claude Code Version

2.1.44

Platform

Anthropic API

Operating System

Windows

Terminal/Shell

Cursor

Additional Information

_No response_