[BUG] [BUG] Claude for Desktop 2000px screenshot limit breaks multi-image conversations

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 using Claude for Desktop (macOS app, version 1.5354.0) and pointing Claude at a folder containing photos and video recordings, the application throws the following error after processing several media files:

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

This makes it impossible to continue working with media folders without losing all context and starting fresh. There's no warning before the failure, and no way to recover within the current session.

What Should Happen?

Claude for Desktop should automatically downscale screenshots to stay within API limits before sending them, or provide a clear warning when adding images that would exceed the dimension limits. The application should handle dimension constraints gracefully without breaking the conversation mid-session.

Error Messages/Logs

An image in the conversation1. Open Claude for Desktop exceeds the dimension limit for many-image requests (2000px). Start a new session with fewer images.

Steps to Reproduce

1. Open Claude for Desktop (macOS app)
2. Point Claude at a folder containing photos and video recordings
3. Claude processes the media files in the folder
4. After processing several files, the error appears: "An image in the conversation exceeds the dimension limit for many-image requests (2000px). Start a new session with fewer images."
5. The conversation becomes blocked and cannot continue without starting a new session

Claude Model

None

Is this a regression?

Yes, this worked in a previous version

Last Working Version

_No response_

Claude Code Version

1.5354.0 (9a9e3d) 2026-04-29T01:14:34.000Z

Platform

Anthropic API

Operating System

macOS

Terminal/Shell

N/A - Using Claude for Desktop app (not a terminal/CLI). This bug is in the Claude Desktop application for macOS, version 1.5354.0 (9a9e3d).

Additional Information

_No response_