[BUG] Session permanently stuck after "image exceeds dimension limit" error in VSCode extension

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?

Once the error "An image in the conversation exceeds the dimension limit for many-image requests (2000px)" appears, the session becomes permanently unusable. Every subsequent message — even plain text like "hi" — returns the same error because the conversation history (including the problematic image) is re-sent with each request.

Steps to reproduce

Send an image in a session in the VSCode extension
Receive the dimension limit error
Type any follow-up message (text only)
Error repeats indefinitely — session cannot continue
Expected behavior
Either: the extension auto-resizes images before sending, OR the session should recover gracefully for text-only follow-up messages.

Actual behavior
Session is permanently broken. Only workaround is opening a new session.

Additional context

Images were 955×1032px (under the 2000px limit), suggesting the error may be triggered by cumulative multi-image context rather than a single oversized image
Extension version: (add yours)
OS: Windows 11

What Should Happen?

Claude should continue responding to text-only messages normally, even after an image-related error. The session should not be permanently broken by a single failed image upload.

Error Messages/Logs

An image in the conversation exceeds the dimension limit for many-image requests (2000px). Start a new session with fewer images.

Steps to Reproduce

1. Open Claude Code in the VSCode extension
2. Send a message that includes an image (955×1032px in this case)
3. Receive the dimension limit error
4. Send any plain text follow-up message (e.g. "continue" or "hi")
5. The same error appears again — session is permanently stuck
6. Only fix is opening a new session entirely

Claude Model

Sonnet (default)

Is this a regression?

Yes, this worked in a previous version

Last Working Version

_No response_

Claude Code Version

2.1.107

Platform

Anthropic API

Operating System

Windows

Terminal/Shell

Windows Terminal

Additional Information

The images involved were 955×1032px — technically under the 2000px limit. The error may be triggered by cumulative multi-image conversation history rather than a single oversized image. The session cannot recover even for text-only messages after the error occurs.