[Bug] Auto-Compact failed to trigger

Question

**Bug Description**
autocompact failed to trigger

This is just, odd... Claude was working and I confirmed autocompact was enabled, but it eventually got stuck, said context was too low to continue, and that I should run autocompact. I then couldn't manually run `/compact` because the conversation was too long??

**Environment Info**
- Platform: darwin
- Terminal: Apple_Terminal
- Version: 2.0.69
- Feedback ID: b09a50fd-c244-4eef-ada1-6e2797588df6

**Errors**
```json
[]
```