[Bug] Auto-compact not triggering despite being enabled, causing context limit errors

Bug Description
Again my sessions usually auto compact but this time they are not auto compacting and I'm getting this error of context limit reset. I checked my setup config and it says I have auto compact enabled so I'm not sure what's going on.

Environment Info

• Platform: darwin
• Terminal: ghostty
• Version: 2.1.56
• Feedback ID: 0cce78a9-56c3-446f-9395-c64870f774a3

Errors

[{"error":"Error: NON-FATAL: Lock acquisition failed for /Users/victorpaytuvi/.local/share/claude/versions/2.1.56 (expected in multi-process scenarios)\n    at pPR (/$bunfs/root/claude:3631:2100)\n    at HvA (/$bunfs/root/claude:3631:1211)\n    at processTicksAndRejections (native:7:39)","timestamp":"2026-02-25T17:48:14.973Z"},{"error":"Error\n    at jKR (/$bunfs/root/claude:1926:11175)\n    at async $9B (/$bunfs/root/claude:1934:378)\n    at async yv7 (/$bunfs/root/claude:1934:8500)\n    at processTicksAndRejections (unknown:7:39)","timestamp":"2026-02-25T17:48:16.348Z"},{"error":"Error: Plugin Notion has an invalid manifest file at /Users/victorpaytuvi/.claude/plugins/cache/claude-plugins-official/Notion/0.1.0/.claude-plugin/plugin.json.\n\nValidation errors: : Unrecognized keys: \"category\", \"source\"\n\nPlease fix the manifest or remove it. The plugin cannot load with an invalid manifest.\n    at jKR (/$bunfs/root/claude:1926:11175)\n    at async $9B (/$bunfs/root/claude:1934:378)\n    at async yv7 (/$bunfs/root/claude:1934:8500)\n    at processTicksAndRejections (native:7:39)","timestamp":"2026-02-25T17:48:16.348Z"},{"error":"Error: File does not exist. Note: your current working directory is /Users/victorpaytuvi/Desktop/SecondBrain.\n    at call (/$bunfs/root/claude:1792:6346)\n    at async vQ8 (/$bunfs/root/claude:3470:15034)\n    at processTicksAndRejections (native:7:39)","timestamp":"2026-02-25T17:48:49.513Z"},{"error":"Error: EISDIR: illegal operation on a directory, read '/Users/victorpaytuvi/Desktop/CLAUDE-PROJECTS/intelligems-report-builder'\n    at No_ (/$bunfs/root/claude:1646:248)\n    at processTicksAndRejections (native:7:39)","timestamp":"2026-02-25T17:50:14.153Z"},{"error":"Error: EISDIR: illegal operation on a directory, read '/Users/victorpaytuvi/Desktop/CLAUDE-PROJECTS/intelligems-report-builder/node_modules/@anthropic-ai/claude-agent-sdk'\n    at No_ (/$bunfs/root/claude:1646:248)\n    at processTicksAndRejections (native:7:39)","timestamp":"2026-02-25T17:53:35.947Z"},{"error":"Error: File does not exist. Note: your current working directory is /Users/victorpaytuvi/Desktop/SecondBrain.\n    at call (/$bunfs/root/claude:1792:6346)\n    at async vQ8 (/$bunfs/root/claude:3470:15034)\n    at processTicksAndRejections (native:7:39)","timestamp":"2026-02-25T19:10:50.995Z"},{"error":"Error: 400 {\"type\":\"error\",\"error\":{\"type\":\"invalid_request_error\",\"message\":\"prompt is too long: 210584 tokens > 180000 maximum\"},\"request_id\":\"req_011CYVLagFiz7LtHnuwSjZTB\"}\n    at generate (/$bunfs/root/claude:267:28317)\n    at makeRequest (/$bunfs/root/claude:306:5435)\n    at processTicksAndRejections (native:7:39)","timestamp":"2026-02-25T19:27:38.121Z"},{"error":"Error: Tool ToolSearch not found\n    at XOB (/$bunfs/root/claude:2360:7832)\n    at P8 (/$bunfs/root/claude:226:20799)\n    at $6 (/$bunfs/root/claude:226:39202)\n    at Qw (/$bunfs/root/claude:226:49828)\n    at Uu (/$bunfs/root/claude:226:86100)\n    at jRT (/$bunfs/root/claude:226:85072)\n    at ml (/$bunfs/root/claude:226:84896)\n    at Qh (/$bunfs/root/claude:226:81317)\n    at fR (/$bunfs/root/claude:226:6408)\n    at mT (/$bunfs/root/claude:226:4905)","timestamp":"2026-02-25T19:27:53.805Z"},{"error":"Error: Tool ToolSearch not found\n    at XOB (/$bunfs/root/claude:2360:7832)\n    at P8 (/$bunfs/root/claude:226:20799)\n    at $6 (/$bunfs/root/claude:226:39202)\n    at Qw (/$bunfs/root/claude:226:49828)\n    at Uu (/$bunfs/root/claude:226:86100)\n    at jRT (/$bunfs/root/claude:226:85072)\n    at ml (/$bunfs/root/claude:226:84896)\n    at Qh (/$bunfs/root/claude:226:81317)\n    at fR (/$bunfs/root/claude:226:6408)\n    at mT (/$bunfs/root/claude:226:4905)","timestamp":"2026-02-25T19:27:53.812Z"},{"error":"Error: Request was aborted.\n    at ehR (/$bunfs/root/claude:819:96594)\n    at next (native:1:11)\n    at pR0 (/$bunfs/root/claude:5992:6662)\n    at next (native:1:11)\n    at nR0 (/$bunfs/root/claude:5997:9142)\n    at processTicksAndRejections (native:7:39)","timestamp":"2026-02-25T19:32:57.732Z"},{"error":"RangeError: path should be a `path.relative()`d string, but got \"..\"\n    at IK7 (/$bunfs/root/claude:820:5386)\n    at gm (/$bunfs/root/claude:820:5559)\n    at _tes…

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