Hi Sam
Based on your testing, this does not appear to be a problem with the Windows Server itself, it points more toward a Windows App for macOS client issue or a compatibility/network handling issue within the app itself rather than an RDP configuration problem on the server. Similar reports of intermittent 0x204 errors on macOS have been discussed by other users using Microsoft Remote Desktop/Windows App for Mac.
A few things worth checking:
- In Windows App, delete the saved PC entry and recreate it from scratch.
- Try connecting using both the IP address and the hostname (if available).
- Disable any saved Gateway configuration if you are connecting directly.
- Check whether macOS is changing network priority (Wi‑Fi, VPN, Ethernet, etc.), as this has been identified as a cause of some Mac-specific 0x204 issues.
- Verify you are running the latest version of Windows App from the Mac App Store.
- When the failure occurs, try opening a Terminal on the Mac and test whether the RDP port is reachable from that Mac at the same time. If the port is reachable but Windows App still fails while the third-party client connects, that further points to a Windows App issue.
Since you've already reinstalled the app, cleared caches, and confirmed that another RDP client works consistently, I would suggest submitting feedback from within Windows App and opening a support case with Microsoft, as this may require investigation of the macOS client logs.