[Bug] Multiple screenshots trigger image limit error with poor UX for recovery

Bug Description
placing two screenshots or more in a message triggers the 'image has exceeded the limit' dialog... this makes it impossible to continue. We need options to remove old screenshots so the message can go through, I can't undo my message easily and resend... its just poor UX to have to retype all of my message and re-screenshot things.

Environment Info

• Platform: darwin
• Terminal: vscode
• Version: 2.1.118
• Feedback ID: 220373bb-021a-4480-bc96-41f88d4dbacf

Errors

[{"error":"Error: NON-FATAL: Lock acquisition failed for /Users/treycollins/.local/share/claude/versions/2.1.118 (expected in multi-process scenarios)\n    at ai_ (/$bunfs/root/src/entrypoints/cli.js:2756:2177)\n    at IK8 (/$bunfs/root/src/entrypoints/cli.js:2756:1257)\n    at processTicksAndRejections (native:7:39)","timestamp":"2026-04-23T16:56:17.759Z"},{"error":"Error: File does not exist. Note: your current working directory is /Users/treycollins/Dropbox/DesignTools.\n    at call (/$bunfs/root/src/entrypoints/cli.js:4709:7645)\n    at processTicksAndRejections (native:7:39)","timestamp":"2026-04-23T16:59:55.218Z"},{"error":"Error: File does not exist. Note: your current working directory is /Users/treycollins/Dropbox/DesignTools.\n    at call (/$bunfs/root/src/entrypoints/cli.js:4709:7645)\n    at processTicksAndRejections (native:7:39)","timestamp":"2026-04-23T16:59:55.563Z"},{"error":"Error: Request was aborted.\n    at makeRequest (/$bunfs/root/src/entrypoints/cli.js:50:3448)\n    at processTicksAndRejections (native:7:39)","timestamp":"2026-04-24T01:13:08.820Z"},{"error":"AxiosError: timeout of 5000ms exceeded\n    at <anonymous> (/$bunfs/root/src/entrypoints/cli.js:115:13291)\n    at emit (node:events:92:22)\n    at <anonymous> (/$bunfs/root/src/entrypoints/cli.js:114:3321)\n    at request (/$bunfs/root/src/entrypoints/cli.js:117:2467)\n    at processTicksAndRejections (native:7:39)","timestamp":"2026-04-24T04:06:55.259Z"},{"error":"AxiosError: timeout of 5000ms exceeded\n    at <anonymous> (/$bunfs/root/src/entrypoints/cli.js:115:13291)\n    at emit (node:events:92:22)\n    at <anonymous> (/$bunfs/root/src/entrypoints/cli.js:114:3321)\n    at request (/$bunfs/root/src/entrypoints/cli.js:117:2467)\n    at processTicksAndRejections (native:7:39)","timestamp":"2026-04-24T14:27:17.423Z"},{"error":"Error: 400 {\"type\":\"error\",\"error\":{\"type\":\"invalid_request_error\",\"message\":\"messages.32.content.1.image.source.base64.data: At least one of the image dimensions exceed max allowed size for many-image requests: 2000 pixels\"},\"request_id\":\"req_011CaNqZFEb4ZzFKidspXcSD\"}\n    at generate (/$bunfs/root/src/entrypoints/cli.js:11:54964)\n    at makeRequest (/$bunfs/root/src/entrypoints/cli.js:50:4943)\n    at processTicksAndRejections (native:7:39)","timestamp":"2026-04-24T15:32:21.724Z"}]