[Bug] Image Upload Fails with 400 Error on Large Image Files

Bug Description
If you add a image thats too big it bricks claude code it seems throwing 400s after its been added even after for all new messages

Environment Info

• Platform: darwin
• Terminal: Apple_Terminal
• Version: 2.0.1
• Feedback ID: f82c6c5b-f3d1-48e3-bb15-597c335a68e0

Errors

[{"error":"Error: Language not supported while highlighting code, falling back to markdown: \n    at $z (/$bunfs/root/claude:1599:1192)\n    at map (native:1:11)\n    at d7 (/$bunfs/root/claude:1599:905)\n    at tGW (/$bunfs/root/claude:2765:9386)\n    at Kw (/$bunfs/root/claude:36:19415)\n    at $d (/$bunfs/root/claude:38:42805)\n    at u5 (/$bunfs/root/claude:38:38347)\n    at Hj (/$bunfs/root/claude:38:38275)\n    at Nw (/$bunfs/root/claude:38:38129)\n    at xF (/$bunfs/root/claude:38:35208)","timestamp":"2025-11-12T19:25:05.549Z"},{"error":"Error: Web search error: unavailable\n    at Qy9 (/$bunfs/root/claude:3213:2718)\n    at call (/$bunfs/root/claude:3213:5429)\n    at processTicksAndRejections (native:7:39)","timestamp":"2025-11-12T19:27:07.310Z"},{"error":"Error: Language not supported while highlighting code, falling back to markdown: \n    at $z (/$bunfs/root/claude:1599:1192)\n    at map (native:1:11)\n    at d7 (/$bunfs/root/claude:1599:905)\n    at tGW (/$bunfs/root/claude:2765:9386)\n    at Kw (/$bunfs/root/claude:36:19415)\n    at $d (/$bunfs/root/claude:38:42805)\n    at u5 (/$bunfs/root/claude:38:38347)\n    at Hj (/$bunfs/root/claude:38:38275)\n    at Nw (/$bunfs/root/claude:38:38129)\n    at xF (/$bunfs/root/claude:38:35208)","timestamp":"2025-11-12T19:44:23.331Z"},{"error":"Error: Language not supported while highlighting code, falling back to markdown: \n    at $z (/$bunfs/root/claude:1599:1192)\n    at map (native:1:11)\n    at d7 (/$bunfs/root/claude:1599:905)\n    at tGW (/$bunfs/root/claude:2765:9386)\n    at Kw (/$bunfs/root/claude:36:19415)\n    at $d (/$bunfs/root/claude:38:42805)\n    at u5 (/$bunfs/root/claude:38:38347)\n    at Hj (/$bunfs/root/claude:38:38275)\n    at Nw (/$bunfs/root/claude:38:38129)\n    at xF (/$bunfs/root/claude:38:35208)","timestamp":"2025-11-12T19:46:10.556Z"},{"error":"Error: Language not supported while highlighting code, falling back to markdown: \n    at $z (/$bunfs/root/claude:1599:1192)\n    at map (native:1:11)\n    at d7 (/$bunfs/root/claude:1599:905)\n    at tGW (/$bunfs/root/claude:2765:9386)\n    at Kw (/$bunfs/root/claude:36:19415)\n    at $d (/$bunfs/root/claude:38:42805)\n    at u5 (/$bunfs/root/claude:38:38347)\n    at Hj (/$bunfs/root/claude:38:38275)\n    at Nw (/$bunfs/root/claude:38:38129)\n    at xF (/$bunfs/root/claude:38:35208)","timestamp":"2025-11-12T19:46:10.557Z"},{"error":"Error: Language not supported while highlighting code, falling back to markdown: \n    at $z (/$bunfs/root/claude:1599:1192)\n    at map (native:1:11)\n    at d7 (/$bunfs/root/claude:1599:905)\n    at tGW (/$bunfs/root/claude:2765:9386)\n    at Kw (/$bunfs/root/claude:36:19415)\n    at $d (/$bunfs/root/claude:38:42805)\n    at u5 (/$bunfs/root/claude:38:38347)\n    at Hj (/$bunfs/root/claude:38:38275)\n    at Nw (/$bunfs/root/claude:38:38129)\n    at xF (/$bunfs/root/claude:38:35208)","timestamp":"2025-11-12T19:46:10.557Z"},{"error":"Error: Language not supported while highlighting code, falling back to markdown: \n    at $z (/$bunfs/root/claude:1599:1192)\n    at map (native:1:11)\n    at d7 (/$bunfs/root/claude:1599:905)\n    at tGW (/$bunfs/root/claude:2765:9386)\n    at Kw (/$bunfs/root/claude:36:19415)\n    at $d (/$bunfs/root/claude:38:42805)\n    at u5 (/$bunfs/root/claude:38:38347)\n    at Hj (/$bunfs/root/claude:38:38275)\n    at Nw (/$bunfs/root/claude:38:38129)\n    at xF (/$bunfs/root/claude:38:35208)","timestamp":"2025-11-12T19:46:10.557Z"},{"error":"Error: Request was aborted.\n    at new W5 (unknown:1:28)\n    at new _Y (/$bunfs/root/claude:716:20515)\n    at new F2 (/$bunfs/root/claude:716:21301)\n    at makeRequest (/$bunfs/root/claude:871:3864)\n    at processTicksAndRejections (native:7:39)","timestamp":"2025-11-12T19:46:54.529Z"},{"error":"Error: Language not supported while highlighting code, falling back to markdown: \n    at $z (/$bunfs/root/claude:1599:1192)\n    at map (native:1:11)\n    at d7 (/$bunfs/root/claude:1599:905)\n    at tGW (/$bunfs/root/claude:2765:9386)\n    at Kw (/$bunfs/root/claude:36:19415)\n    at $d (/$bunfs/root/claude:38:42805)\n    at u5 (/$bunfs/root/claude:38:38347)\n    at Hj (/$bunfs/root/claude:38:38275)\n    at Nw (/$bunfs/

Note: Error logs were truncated.