[BUG] Improve UX for large image handling - unhelpful repeated error message

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?

Description:
Problem
When attempting to paste/include a large image in Claude Code, the CLI displays:
Image was too large. Double press esc to go back and try again with a smaller image.
This message repeats identically on subsequent attempts, even when asking Claude to resize the image or handle it differently.
Current behavior

Same error message loops indefinitely
No indication of actual size limits or thresholds
Claude cannot resize the image itself despite being asked to
User is stuck without clear guidance

Currently users must manually resize or base64 encode:

Opus 4.5
MAC OS - Tahoe 26.1
Terminal

What Should Happen?

Expected behavior
Any of these would be better:

Auto-resize images that exceed display limits (with user confirmation)
Provide actual size limits in the error message (e.g., "Image exceeds 2MB / 2048px limit")
Offer actionable alternatives ("Would you like me to process this via base64 encoding?")
Accept the image for processing even if it can't be rendered inline in terminal

Workaround

Error Messages/Logs

Steps to Reproduce

add an large img to terminal

Claude Model

None

Is this a regression?

Yes, this worked in a previous version

Last Working Version

_No response_

Claude Code Version

4.5

Platform

Anthropic API

Operating System

macOS

Terminal/Shell

Terminal.app (macOS)

Additional Information

_No response_