[BUG] Critical: Context low when context available, compact, message does not work after this.

Environment

• Platform (select one):
• [x] Anthropic API
• [ ] AWS Bedrock
• [ ] Google Vertex AI
• [x] Other: Max Plan
• Claude CLI version: 1.0.62
• Operating System: MacOS Sequoia 15.0.1
• Terminal: VS code integrated terminal

Bug Description

Context low when context is actually available

Steps to Reproduce

1. Use tasks and reach somehow till 1 digit context
2. Then send some messages asking questions
3. Quit
4. continue

Expected Behavior

To be able to send messages

Actual Behavior

> Okay, create tasks to fix the tests systematically
  ⎿  Context low · Run /compact to compact & continue

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

> /bug 
  ⎿  Error submitting bug report

╭───────────────────────────────────────────────────────────────────╮
│ >                                                                 │
╰───────────────────────────────────────────────────────────────────╯
  ? for shortcuts                                ⧉ In test_leave.py
                                              Bypassing Permissions
                                Context left until auto-compact: 9%

Additional Context

This happens after some Task(s) I kill claude and start again with --continue.

Active reported bugs:

• Bug reporting does not work. ( This one is annoying )
• Updating CLAUDE.md with # {message} crashes cli ( This one is annoying, but workable )

Unreported:

• Hangs after longer usage, gets very very slow