[Bug] Auto-Compact not triggering before context overflow

Bug Description
currently the context overflow often stopps and I need to delete some of the conversation… 'autocompact' doesn't work as well as last month

Environment Info

• Platform: darwin
• Terminal: WarpTerminal
• Version: 2.1.34
• Feedback ID: 1cc881af-1870-4cb6-a1b8-ca0cd4449f89

Errors

[{"error":"Error: 400 {\"type\":\"error\",\"error\":{\"type\":\"invalid_request_error\",\"message\":\"messages.89.content.11.image.source.base64.data: At least one of the image dimensions exceed max allowed size for many-image requests: 2000 pixels\"},\"request_id\":\"req_011CXtwbqGBCmAXM4PdL5nTy\"}\n    at generate (/$bunfs/root/claude:319:8796)\n    at makeRequest (/$bunfs/root/claude:336:5435)\n    at processTicksAndRejections (native:7:39)","timestamp":"2026-02-07T15:26:06.229Z"},{"error":"Error: EISDIR: illegal operation on a directory, read\n    at readFileSync (unknown)\n    at <anonymous> (/$bunfs/root/claude:12:742)\n    at iC (/$bunfs/root/claude:11:49098)\n    at readFileSync (/$bunfs/root/claude:12:701)\n    at EzB (/$bunfs/root/claude:6102:17996)\n    at call (/$bunfs/root/claude:3269:2356)\n    at call (/$bunfs/root/claude:3265:8804)\n    at l38 (/$bunfs/root/claude:3447:13995)\n    at processTicksAndRejections (native:7:39)","timestamp":"2026-02-07T15:28:09.228Z"},{"error":"AbortError: The operation was aborted.\n    at unknown\n    at abortChildProcess (node:child_process:935:42)\n    at onAbortListener2 (node:child_process:35:24)\n    at abort (unknown)\n    at <anonymous> (/$bunfs/root/claude:6109:2200)","timestamp":"2026-02-07T15:30:59.545Z"},{"error":"Error: ENOENT: no such file or directory, open '/element_closed.png'\n    at readFileSync (unknown)\n    at <anonymous> (/$bunfs/root/claude:12:846)\n    at iC (/$bunfs/root/claude:11:49098)\n    at readFileBytesSync (/$bunfs/root/claude:12:800)\n    at pE_ (/$bunfs/root/claude:889:5409)\n    at processTicksAndRejections (native:7:39)","timestamp":"2026-02-07T15:33:21.527Z"},{"error":"Error: ENOENT: no such file or directory, open '/element_closed.png'\n    at readFileSync (unknown)\n    at <anonymous> (/$bunfs/root/claude:12:846)\n    at iC (/$bunfs/root/claude:11:49098)\n    at readFileBytesSync (/$bunfs/root/claude:12:800)\n    at pE_ (/$bunfs/root/claude:889:5409)\n    at processTicksAndRejections (native:7:39)","timestamp":"2026-02-07T15:33:24.630Z"},{"error":"Error: Request was aborted.\n    at makeRequest (/$bunfs/root/claude:336:3940)\n    at processTicksAndRejections (native:7:39)","timestamp":"2026-02-07T15:35:47.619Z"},{"error":"Error: Request was aborted.\n    at K6R (/$bunfs/root/claude:841:99554)\n    at DaB (/$bunfs/root/claude:5680:2067)\n    at processTicksAndRejections (native:7:39)","timestamp":"2026-02-07T15:35:47.628Z"},{"error":"Error: Compaction interrupted · This may be due to network issues — please try again.\n    at VzB (/$bunfs/root/claude:3273:5277)\n    at async sQT (/$bunfs/root/claude:3271:267)\n    at async HfB (/$bunfs/root/claude:3356:2545)\n    at processTicksAndRejections (native:7:39)","timestamp":"2026-02-07T15:35:47.629Z"},{"error":"Error: Request was aborted.\n    at K6R (/$bunfs/root/claude:841:99554)\n    at DaB (/$bunfs/root/claude:5680:2067)\n    at processTicksAndRejections (native:7:39)","timestamp":"2026-02-07T15:35:47.634Z"},{"error":"Error: Request was aborted.\n    at K6R (/$bunfs/root/claude:841:99554)\n    at _aB (/$bunfs/root/claude:5675:4372)\n    at DaB (/$bunfs/root/claude:5680:7410)\n    at processTicksAndRejections (native:7:39)","timestamp":"2026-02-07T15:36:54.150Z"},{"error":"Error: Request was aborted.\n    at K6R (/$bunfs/root/claude:841:99554)\n    at DaB (/$bunfs/root/claude:5680:2067)\n    at processTicksAndRejections (native:7:39)","timestamp":"2026-02-07T15:36:54.158Z"},{"error":"Error: Compaction interrupted · This may be due to network issues — please try again.\n    at VzB (/$bunfs/root/claude:3273:5277)\n    at async sQT (unknown)\n    at async HfB (unknown)\n    at processTicksAndRejections (native:7:39)","timestamp":"2026-02-07T15:36:54.159Z"},{"error":"Error: Request was aborted.\n    at K6R (/$bunfs/root/claude:841:99554)\n    at DaB (/$bunfs/root/claude:5680:2067)\n    at processTicksAndRejections (native:7:39)","timestamp":"2026-02-07T15:36:54.164Z"},{"error":"Error: 400 {\"type\":\"error\",\"error\":{\"type\":\"invalid_request_error\",\"message\":\"prompt is too long: 203616 tokens > 200000 maximum\"},\"request_id\":\"req_011CXtxaw5m9u3jS6eHiXZ5m\"}\n    at generate (/$bunfs/root/claude:319:8796)\n    at makeRequest (/$bunfs/root/claude:336:5435)\n    at processTicksAndRejections (native…

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