[BUG] [Regression] Image size limit dropped from 5MB to ~3.2MB around Dec 14, causing session-breaking failures

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?

Since approximately December 14, 2025, Claude Code is rejecting images that previously worked fine. The enforced limit appears to have dropped from the documented 5MB to approximately 3.2-3.3MB. When an "oversized" image enters the session, all subsequent API calls fail with no recovery option.

Evidence of Regression

• Before Dec 14: Standard macOS screenshots (3-4MB) loaded without issues
• After Dec 14: Same types of screenshots now trigger "Image too large" errors
• No changes to workflow or image sources on user's end

Two Bugs

1. Undocumented limit reduction: The actual limit is ~35% lower than documented
2. No recovery mechanism: Once an oversized image enters the session:

• All subsequent API calls fail
• /clear does not remove the image from context
• Session becomes permanently unusable
• Only workaround: manually delete session file

What Should Happen?

Loading images via either grab and drop into terminal or by providing file path equally fail. Should load. Have loaded routinely in the past.

Suggested Fixes

1. Immediate: Restore the 5MB limit or update documentation to reflect actual limit
2. Validation: Reject oversized images before adding to conversation context
3. Recovery: Add command to remove last message/attachment from context

Error Messages/Logs

image too large. Try loading smaller image.

Steps to Reproduce

Steps to Reproduce

1. Start Claude Code session
2. Provide path to any image between 3.3-5 MB
3. Session accepts the image
4. All subsequent interactions fail
5. No way to recover the session

Environment

• Claude Code version: 2.0.70
• OS: macOS Darwin 24.6.0
• Model: Opus 4.5

Related Issues

• #8202 - Image Exceeds 5 MB Size Limit breaks session

Claude Model

Opus

Is this a regression?

Yes, this worked in a previous version

Last Working Version

_No response_

Claude Code Version

2.0.70

Platform

Anthropic API

Operating System

macOS

Terminal/Shell

Terminal.app (macOS)

Additional Information

Test Image Properties

The failing image was a standard macOS screenshot:

• Dimensions: 2364 × 1662 (well under 8000 × 8000 limit)
• Format: PNG, 8-bit/color RGBA, non-interlaced
• File size: 3,684,646 bytes (3.51 MB)

Multiple images were trialed and all of similar or larger sized triggered the fault.