[BUG] Oversized image breaks conversation permanently - no way to recover without starting new chat

[precisionpete]

Preflight Checklist

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

What's Wrong?

When a user pastes an image that exceeds the dimension limits (>2000px for many-image requests), the API returns a 400 error. However, the oversized image remains in the conversation history, causing all subsequent requests to fail with the same error - even plain text messages with no images attached.

What Should Happen?

One or more of the following should happen:

• Option A: Validate image dimensions at paste/upload time and reject before adding to conversation
• Option B: Provide UI to remove the offending image from conversation history
• Option C: Exclude failed images from being resubmitted in subsequent requests
• Option D: Display clear error with actionable recovery steps

Error Messages/Logs

API Error: 400 {"type":"error","error":{"type":"invalid_request_error","message":"messages.100.content.2.image.source.base64.data: At least one of the image dimensions exceed max allowed size for many-image requests: 2000 pixels"},"request_id":"req_011CVwMREcResPJWSbJmcuri"}

Steps to Reproduce

1. Paste a large image (e.g., >2000px on any dimension) into Claude Code
2. Send the message - receive error: messages.X.content.0.image.source.base64.data: At least one of the image dimensions exceed max allowed size for many-image requests: 2000 pixels
3. Try to send a plain text message (no image)
4. Same error occurs on every subsequent request

Claude Model

Opus

Is this a regression?

Yes, this worked in a previous version

Last Working Version

No response

Claude Code Version

2.0.28 (Claude Code)

Platform

Anthropic API

Operating System

Ubuntu/Debian Linux

Terminal/Shell

VS Code integrated terminal

Additional Information

Suggested Fixes

1. Immediate: Validate image dimensions before adding to conversation
2. Short-term: Add UI control to remove messages/images from conversation history
3. Long-term: Implement automatic retry without failed images, or client-side image resizing

Workaround

Currently, users must start a new conversation and manually reconstruct any important context.

[github-actions]

Found 3 possible duplicate issues:

1. [Bug] Anthropic API Error: Image dimensions exceed max allowed size (8000 pixels) #12351
2. [Bug] Anthropic API Error: Image dimensions exceed max allowed size in multi-image requests #12867
3. [BUG] Stuck in failure loop due to invalid image file #13341

This issue will be automatically closed as a duplicate in 3 days.

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🤖 Generated with Claude Code

[peterHoburg]

I am having the same issue.

[DawidBester]

Also experiencing the same issue, after error chat cannot be continued: ⎿ API Error: 400
{"type":"error","error":{"type":"invalid_request_error","message":"messages.0.content.3.image.source.base64.data:
At least one of the image dimensions exceed max allowed size: 8000
pixels"