[BUG] Oversized image blocks all subsequent messages in a conversation

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?

When uploading an image larger than the allowed size in Claude Code VS Extension, the request is correctly blocked with an “Image base64 size (XX MB) exceeds API limit (5.0 MB). Please resize the image before sending.” error.
However, every subsequent message in the same conversation is also blocked with the same error -> even if it’s only text (with no message whatsoever)

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What Should Happen?

The oversized image should be rejected, but subsequent text messages in the conversation should work normally.

Error Messages/Logs

Steps to Reproduce

Start a new conversation through Claude Code VS Extension.

Upload an image that exceeds the size limit.

Receive the "image too large" error.

Send a text-only message in the same conversation.

Get blocked from proceeding with the conversation even when not sending any images (leaving only the option of creating a new conversation from scratch for the user).

Claude Model

Opus

Is this a regression?

I don't know

Last Working Version

_No response_

Claude Code Version

2.1.19

Platform

Anthropic API

Operating System

macOS

Terminal/Shell

Other

Additional Information

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