[BUG] Infinite retry loop when viewing large images in many-image context (2000px limit)

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 a conversation already contains multiple images (15+), attempting to view a large image (>2000px dimension) triggers an API error. Instead of handling this gracefully, Claude Code enters an infinite retry loop with the same failing request.

Error Message:

API Error: 400 {"type":"error","error":{"type":"invalid_request_error", "message":"messages.23.content.5.image.source.base64.data: At least one  of the image dimensions exceed max allowed size for many-image requests: 2000 pixels"}}

What Should Happen?

Claude Code should:

1. Detect the "many-image requests" size limit error
2. Auto-compress the image and retry, OR
3. Provide alternative (metadata/thumbnail), OR
4. Clearly explain the limitation to the user

Instead of silently retrying the same failing request indefinitely.

Error Messages/Logs

API Error: 400 {"type":"error","error":{"type":"invalid_request_error", "message":"messages.23.content.5.image.source.base64.data: At least one  of the image dimensions exceed max allowed size for many-image requests: 2000 pixels"}, "request_id":"req_011CXhNo9yEk1fbuj6JhweZR"}


The same error repeats multiple times with different request_ids, indicating retry attempts.

Steps to Reproduce

1. Start a conversation and use the view tool to load 15+ images
2. Attempt to view a new image with dimensions > 2000px
3. Observe: API returns 400 error
4. Observe: Claude Code retries the same request without any error handling
5. User must manually intervene to break the loop

Claude Model

Opus

Is this a regression?

I don't know

Last Working Version

_No response_

Claude Code Version

Latest (Claude Desktop Mac with Code module)

Platform

Anthropic API

Operating System

macOS

Terminal/Shell

Terminal.app (macOS)

Additional Information

Root Cause Analysis

The API enforces stricter image size limits (2000px max dimension) for "many-image requests" compared to single-image requests. Claude Code does not:

• Track the number of images already in the conversation context
• Handle this specific error type
• Implement any fallback strategy

Suggested Fix

1. Catch invalid_request_error with "many-image requests" in the message
2. Implement auto-compression (resize to <2000px) and retry
3. Or fall back to returning image metadata instead of visual content
4. Add clear user-facing error message explaining the limitation

Related Issue

Related to #22351 but with more specific reproduction steps and error details.