[Bug] Cannot send screenshots after conversation compaction causes unrecoverable state

Bug Description
Just compacted but can't send a simple screenshot and can't seem to recover the conversation without having the same issue

Environment Info

• Platform: darwin
• Terminal: iTerm.app
• Version: 2.0.31
• Feedback ID: 531eba77-3fda-4ded-ad3c-55b762bc945e

Errors

[{"error":"Error: Language not supported while highlighting code, falling back to markdown: \n    at T3 (/$bunfs/root/claude:1120:3185)\n    at map (native:1:11)\n    at kX (/$bunfs/root/claude:1120:2902)\n    at Y6E (/$bunfs/root/claude:1732:6559)\n    at tJ (/$bunfs/root/claude:101:19415)\n    at Rn (/$bunfs/root/claude:103:42816)\n    at z1 (/$bunfs/root/claude:103:38357)\n    at Xg (/$bunfs/root/claude:103:38285)\n    at DK (/$bunfs/root/claude:103:38139)\n    at a6 (/$bunfs/root/claude:103:35218)","timestamp":"2025-11-01T18:43:33.714Z"},{"error":"Error: Language not supported while highlighting code, falling back to markdown: \n    at T3 (/$bunfs/root/claude:1120:3185)\n    at map (native:1:11)\n    at kX (/$bunfs/root/claude:1120:2902)\n    at Y6E (/$bunfs/root/claude:1732:6559)\n    at tJ (/$bunfs/root/claude:101:19415)\n    at Rn (/$bunfs/root/claude:103:42816)\n    at z1 (/$bunfs/root/claude:103:38357)\n    at Xg (/$bunfs/root/claude:103:38285)\n    at DK (/$bunfs/root/claude:103:38139)\n    at a6 (/$bunfs/root/claude:103:35218)","timestamp":"2025-11-01T18:43:33.906Z"},{"error":"Error: 400 {\"type\":\"error\",\"error\":{\"type\":\"invalid_request_error\",\"message\":\"messages.22.content.0.image.source.base64: image exceeds 5 MB maximum: 5418852 bytes > 5242880 bytes\"},\"request_id\":\"req_011CUhfPwngvvfsJr2zLAoCD\"}\n    at generate (/$bunfs/root/claude:381:26098)\n    at makeRequest (/$bunfs/root/claude:526:5345)\n    at processTicksAndRejections (native:7:39)","timestamp":"2025-11-01T18:43:37.672Z"},{"error":"Error: 400 {\"type\":\"error\",\"error\":{\"type\":\"invalid_request_error\",\"message\":\"messages.22.content.0.image.source.base64: image exceeds 5 MB maximum: 5418852 bytes > 5242880 bytes\"},\"request_id\":\"req_011CUhfQFBwsfs665kMeVvoY\"}\n    at generate (/$bunfs/root/claude:381:26098)\n    at makeRequest (/$bunfs/root/claude:526:5345)\n    at processTicksAndRejections (native:7:39)","timestamp":"2025-11-01T18:43:41.737Z"},{"error":"Error: API Error: 400 {\"type\":\"error\",\"error\":{\"type\":\"invalid_request_error\",\"message\":\"messages.22.content.0.image.source.base64: image exceeds 5 MB maximum: 5418852 bytes > 5242880 bytes\"},\"request_id\":\"req_011CUhfQFBwsfs665kMeVvoY\"}\n    at YvH (/$bunfs/root/claude:1732:1535)\n    at async call (/$bunfs/root/claude:1752:12589)\n    at async z8$ (/$bunfs/root/claude:2722:5860)\n    at async n60 (/$bunfs/root/claude:2722:3938)\n    at async hf$ (/$bunfs/root/claude:2828:1785)\n    at async Qy (/$bunfs/root/claude:2826:1796)\n    at async wnH (/$bunfs/root/claude:2828:3664)\n    at async <anonymous> (/$bunfs/root/claude:2836:1418)\n    at async <anonymous> (/$bunfs/root/claude:2821:4671)\n    at processTicksAndRejections (native:7:39)","timestamp":"2025-11-01T18:43:41.747Z"},{"error":"Error: Error during compaction: Error: API Error: 400 {\"type\":\"error\",\"error\":{\"type\":\"invalid_request_error\",\"message\":\"messages.22.content.0.image.source.base64: image exceeds 5 MB maximum: 5418852 bytes > 5242880 bytes\"},\"request_id\":\"req_011CUhfQFBwsfs665kMeVvoY\"}\n    at call (/$bunfs/root/claude:1753:194)\n    at async z8$ (/$bunfs/root/claude:2722:5860)\n    at async n60 (/$bunfs/root/claude:2722:3938)\n    at async hf$ (/$bunfs/root/claude:2828:1785)\n    at async Qy (/$bunfs/root/claude:2826:1796)\n    at async wnH (/$bunfs/root/claude:2828:3664)\n    at async <anonymous> (/$bunfs/root/claude:2836:1418)\n    at async <anonymous> (/$bunfs/root/claude:2821:4671)\n    at processTicksAndRejections (native:7:39)","timestamp":"2025-11-01T18:43:41.748Z"}]