[BUG] PDF too large

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 Claude Code attempts to open a PDF file that exceeds size or page count thresholds, it displays the error message "● PDF too large. Please double press esc to edit your message and try again." However, after this error, Claude Code becomes unresponsive and repeats only this same message for all subsequent inputs, regardless of whether the user follows the instruction or tries different commands.

Steps to Reproduce:

Ask Claude Code to open/read a large PDF file (either by file size or page count)
Receive the "PDF too large" error message
Attempt any subsequent command (including double-pressing ESC to edit the message)
Observe that Claude Code only responds with the same error message

What Should Happen?

After displaying the error, Claude Code should return to normal operation and accept new commands. The error should be a one-time message, not a persistent state.
Actual Behavior:
Claude Code enters an infinite loop where it only outputs "● PDF too large. Please double press esc to edit your message and try again." for all subsequent inputs.

Error Messages/Logs

⎿  Read PDF (433.9KB)

● PDF too large. Please double press esc to edit your message and try again.

> are you broke

● PDF too large. Please double press esc to edit your message and try again.
> What is your favorite color

● PDF too large. Please double press esc to edit your message and try again.

Steps to Reproduce

Ask claude to open a pdf that is either several mb in size (I've had this happen with 4.5mb before) or several hundred pages in length.

Claude Model

Sonnet (default)

Is this a regression?

I don't know

Last Working Version

_No response_

Claude Code Version

2.0.21

Platform

Anthropic API

Operating System

Ubuntu/Debian Linux

Terminal/Shell

WSL (Windows Subsystem for Linux)

Additional Information

_No response_