[Bug] Context lost on "too many images and documents" error

Bug Description
As soon as I hit this too many images
and documents: 101 + 0 > 100" error I loose all the history/context. And I have to start a session from scratch

Environment Info

• Platform: darwin
• Terminal: ghostty
• Version: 2.1.39
• Feedback ID: c487a9c0-6954-4344-bdb0-2c6a88b4b4b4

Errors

[{"error":"Error: NON-FATAL: Lock acquisition failed for /Users/pedroproenca/.local/share/claude/versions/2.1.39 (expected in multi-process scenarios)\n    at wVR (/$bunfs/root/claude:3626:2098)\n    at DjA (/$bunfs/root/claude:3626:1209)\n    at processTicksAndRejections (native:7:39)","timestamp":"2026-02-12T14:05:39.538Z"},{"error":"Error: 400 {\"type\":\"error\",\"error\":{\"type\":\"invalid_request_error\",\"message\":\"too many images and documents: 104 + 0 > 100\"},\"request_id\":\"req_011CY4JxaK5Nj9Ne2KChgJor\"}\n    at generate (/$bunfs/root/claude:319:8796)\n    at makeRequest (/$bunfs/root/claude:358:5435)\n    at processTicksAndRejections (native:7:39)","timestamp":"2026-02-12T14:11:29.004Z"},{"error":"Error: 400 {\"type\":\"error\",\"error\":{\"type\":\"invalid_request_error\",\"message\":\"too many images and documents: 104 + 0 > 100\"},\"request_id\":\"req_011CY4JzpPiQvgRSmBD1t9Mv\"}\n    at generate (/$bunfs/root/claude:319:8796)\n    at makeRequest (/$bunfs/root/claude:358:5435)\n    at processTicksAndRejections (native:7:39)","timestamp":"2026-02-12T14:11:59.549Z"},{"error":"Error: Conversation too long. Press esc twice to go up a few messages and try again.\n    at yhT (/$bunfs/root/claude:3303:939)\n    at async tPB (/$bunfs/root/claude:3388:2545)\n    at processTicksAndRejections (native:7:39)","timestamp":"2026-02-12T14:14:12.034Z"},{"error":"Error: 400 {\"type\":\"error\",\"error\":{\"type\":\"invalid_request_error\",\"message\":\"too many images and documents: 120 + 0 > 100\"},\"request_id\":\"req_011CY4KAfUiKR1uDQft5GFsc\"}\n    at generate (/$bunfs/root/claude:319:8796)\n    at makeRequest (/$bunfs/root/claude:358:5435)\n    at processTicksAndRejections (native:7:39)","timestamp":"2026-02-12T14:14:13.119Z"},{"error":"Error: 400 {\"type\":\"error\",\"error\":{\"type\":\"invalid_request_error\",\"message\":\"too many images and documents: 101 + 0 > 100\"},\"request_id\":\"req_011CY4KgTkrB8MKtpkvrWezQ\"}\n    at generate (/$bunfs/root/claude:319:8796)\n    at makeRequest (/$bunfs/root/claude:358:5435)\n    at processTicksAndRejections (native:7:39)","timestamp":"2026-02-12T14:20:57.284Z"},{"error":"Error: API Error: 400 {\"type\":\"error\",\"error\":{\"type\":\"invalid_request_error\",\"message\":\"too many images and documents: 101 + 0 > 100\"},\"request_id\":\"req_011CY4KgTkrB8MKtpkvrWezQ\"}\n    at yhT (/$bunfs/root/claude:3303:795)\n    at async tPB (unknown)\n    at processTicksAndRejections (native:7:39)","timestamp":"2026-02-12T14:20:57.287Z"},{"error":"Error: 400 {\"type\":\"error\",\"error\":{\"type\":\"invalid_request_error\",\"message\":\"too many images and documents: 101 + 0 > 100\"},\"request_id\":\"req_011CY4KgXfVxk2prfK8xf2Wg\"}\n    at generate (/$bunfs/root/claude:319:8796)\n    at makeRequest (/$bunfs/root/claude:358:5435)\n    at processTicksAndRejections (native:7:39)","timestamp":"2026-02-12T14:20:58.171Z"},{"error":"Error: 400 {\"type\":\"error\",\"error\":{\"type\":\"invalid_request_error\",\"message\":\"too many images and documents: 101 + 0 > 100\"},\"request_id\":\"req_011CY4KiPatJBevSHxys1fg3\"}\n    at generate (/$bunfs/root/claude:319:8796)\n    at makeRequest (/$bunfs/root/claude:358:5435)\n    at processTicksAndRejections (native:7:39)","timestamp":"2026-02-12T14:21:23.414Z"},{"error":"Error: API Error: 400 {\"type\":\"error\",\"error\":{\"type\":\"invalid_request_error\",\"message\":\"too many images and documents: 101 + 0 > 100\"},\"request_id\":\"req_011CY4KiPatJBevSHxys1fg3\"}\n    at yhT (/$bunfs/root/claude:3303:795)\n    at async tPB (/$bunfs/root/claude:3388:2545)\n    at processTicksAndRejections (native:7:39)","timestamp":"2026-02-12T14:21:23.417Z"},{"error":"Error: 400 {\"type\":\"error\",\"error\":{\"type\":\"invalid_request_error\",\"message\":\"too many images and documents: 101 + 0 > 100\"},\"request_id\":\"req_011CY4KiTMM9i8jH98yzrkus\"}\n    at generate (/$bunfs/root/claude:319:8796)\n    at makeRequest (/$bunfs/root/claude:358:5435)\n    at processTicksAndRejections (native:7:39)","timestamp":"2026-02-12T14:21:24.321Z"}]