[BUG] Image Upload Limit API

Preflight Checklist

• [x] I have searched existing issues and this hasn't been reported yet
• [x] This is a single bug report (please file separate reports for different bugs)
• [x] I am using the latest version of Claude Code

What's Wrong?

Whenever I want to upload and send multiple images to claude code for it as reference, the API will often block the screenshots due to them being to large. now it was genuinely not very large images at all, nor very many. This is not a problem in the Web Version nor the App or anywhere else.
Now the other issue is, once that has happened once in that Chat it will block ANY of the next message, making the chat impossible to use thereon after. No matter if I send a smaller image or just a text message.

<img width="848" height="539" alt="Image" src="https://github.com/user-attachments/assets/14635852-5ee7-4514-a5b8-ee05cdd273d9" />

What Should Happen?

The API limit should be significantly larger than 5 MB for images. And more importantly, no later messages should be blocked due to the same problem but the previous image sent should simply be ignored to no longer block responses.

Error Messages/Logs

3 images exceed the API limit (5MB): Image 4: 7.5MB, Image 5: 8.2MB, Image 6: 8.3MB. Please resize these images before sending.

Image base64 size (5.9MB) exceeds API limit (5MB). Please resize the image before sending.

Image base64 size (5.9MB) exceeds API limit (5MB). Please resize the image before sending.

Steps to Reproduce

1. Take screenshot on high resolution screen
2. Upload normally in VS Code Extension / TUI probably too
3. send message
4. See error
5. Try another message without any images
6. See error

Claude Model

None

Is this a regression?

No, this never worked

Last Working Version

_No response_

Claude Code Version

Latest

Platform

Anthropic API

Operating System

Windows

Terminal/Shell

VS Code integrated terminal

Additional Information

_No response_