Using images (like for testing UX changes) often results in the CLI getting into a broken state #4075

Describe the bug

1. Create a UX application with Claud Code CLI
2. Request changes to the UX
3. Ask it to use screenshots to self-validate if the code changes

Eventually you'll start seeing multiple errors on each request like:
"Images and/or native document attachments were removed from the request due to size constraints. Please use smaller image or document files."

I'm guessing it's the large image files sitting in context. not sure how

Affected version

GitHub Copilot CLI 1.0.70-0

Steps to reproduce the behavior

1. Create a UX application with Claud Code CLI
2. Request changes to the UX
3. Ask it to use screenshots to self-validate if the code changes

Eventually you'll start seeing multiple errors on each request like:
"Images and/or native document attachments were removed from the request due to size constraints. Please use smaller image or document files."

Expected behavior

CLI should manage image context aggrressively, using compression, compaction, etc before showing error message.

Additional context

No response