[BUG] Dispatch photo uploads from iPhone silently fail — files never arrive in Cowork desktop session

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?

Photos sent from the iPhone Claude app via Dispatch appear to send successfully on the mobile side (no error shown), but never appear in the active Cowork desktop session. Happens consistently across multiple attempts.
Steps to Reproduce:

Open Cowork on Claude Desktop (Windows, active session)
Open Claude app on iPhone, open Dispatch
Select and send 1–2 photos from Camera Roll
Observe: iPhone shows photos as sent; Cowork desktop receives nothing

Expected: Photos appear in the Cowork session.
Actual: No files arrive. No error on either device. Silent failure.
System Info:

iPhone 15 Pro, latest iOS
Claude Desktop for Windows, latest version
Subscription: Max

Additional Notes:
iPhone default photo format is HEIC. Unknown whether format or file size contributes, but the silent failure with zero error feedback is the core issue — the user has no way to know something went wrong.

What Should Happen?

photos uploaded via dispatch should show up on Claude desktop

Error Messages/Logs

Steps to Reproduce

Steps to Reproduce:

Open Cowork on Claude Desktop (Windows, active session)
Open Claude app on iPhone, open Dispatch
Select and send 1–2 photos from Camera Roll
Observe: iPhone shows photos as sent; Cowork desktop receives nothing

Claude Model

None

Is this a regression?

Yes, this worked in a previous version

Last Working Version

_No response_

Claude Code Version

Version 1.1.8629 (befdfc)

Platform

Anthropic API

Operating System

Windows

Terminal/Shell

Other

Additional Information

_No response_