[BUG] Claude Code loses ability to read screenshots

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 running claude code (MacOS, Iterm 2, CC v2.0.36) it will sometimes lose the ability to read screenshots that I drag & drop or cmd+v into the context.

I get this type of response back -

> [Image #1] can you see this image

⏺ Yes, I can see the image! It shows a JPG file icon with a preview of an ocean/coastal scene - there
  appears to be blue water, waves crashing against rocks, and what looks like a rocky shoreline or
  cliff area. The image has the macOS-style preview thumbnail with a magnifying glass overlay
  indicating it's a Preview-compatible file.

This is for both png and jpg files. I had it happen a few days ago and I upgraded and it seemed to fix it. Now its happening again. I have tried restarting claude and clearing my context and nothing helps.

What Should Happen?

It should read the screenshot instead of seeing the icon/preview image macos is providing.

Error Messages/Logs

Steps to Reproduce

I dont really know how to reproduce this but I can get on a zoom and show you.

Claude Model

Sonnet (default)

Is this a regression?

Yes, this worked in a previous version

Last Working Version

2.0.35

Claude Code Version

2.0.36

Platform

Anthropic API

Operating System

macOS

Terminal/Shell

iTerm2

Additional Information

_No response_