[BUG] Per-image 2000px limit is undocumented and fails mid-session with no recovery

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?

Hitting this error at 40% context window usage: "An image in the conversation exceeds the dimension limit for many-image requests (2000px). Start a new session with fewer images."

Three problems:

• The 2000px per-image cap is not surfaced anywhere in the UI before it fails. Users discover it by losing a session.
• The only remediation offered is "start a new session" — there is no option to drop, downscale, or replace the offending image in place.
• It's triggered by image dimensions, not context size, so the context meter gives zero warning.

Net-net: either auto-downscale images to the cap on upload, warn at paste time, or expose the per-image limit in the context indicator. Forcing a full session restart for a screenshot that's a few hundred pixels too wide is a bad default and a horrible user experience!!!!!

What Should Happen?

Net-net: either auto-downscale images to the cap on upload, warn at paste time, or expose the per-image limit in the context indicator. Forcing a full session restart for a screenshot that's a few hundred pixels too wide is a bad default and a horrible user experience!!!!!

Error Messages/Logs

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

Steps to Reproduce

pasted a f-ing screen shot.

this bug reporting is laborious and also a bad customer experience!!!!

Claude Model

Opus

Is this a regression?

I don't know

Last Working Version

_No response_

Claude Code Version

Version 1.3109.0 (35cbf6)

Platform

Anthropic API

Operating System

macOS

Terminal/Shell

Terminal.app (macOS)

Additional Information

This bug reporting process is horrible! Make someone REALLY work at providing you information...yeah that's a great customer experience.