[Feature/Bug]: File attachments still not working with Windows client and macOS remote server #28559

Problem or use case

Following up on #22320 and the fix introduced in #25146.

I'm using Orca Desktop on Windows as my primary interface, connected to a remote Orca server running on macOS.
Unfortunately, I'm still unable to attach images or files to chat sessions running on the remote Mac.

My setup:

Client: Windows PC (Orca Desktop)
Server: macOS (Remote Orca Server)

Client version: 1.4.224
Server version: 1.4.224

Expected behaviour

I should be able to paste screenshots, drag and drop images, or attach files directly from my Windows PC into a chat running on the remote Mac.

Orca should automatically transfer the attachments to the remote server so the agent can access them, without requiring me to manually copy files between machines.

Current behaviour

Attachments are still not working in my remote chat sessions, despite the original issue being marked as resolved.

Proposed solution

I'd love to see attachment support work consistently across all remote chat types, including Windows-to-macOS connections.

If this is already intended to work in structured chat, it would be great to investigate whether there's a cross-platform issue affecting Windows clients.

This is an important part of my workflow, as I primarily use my Windows PC to interact with agents running on my Mac.

Thanks for looking into this!

Alternatives or additional context

No response