My Windows 365 Cloud PC displays a black screen when I try to connect, followed by this message: "Your Remote Desktop Services session has ended. The administrator has ended the session, an error occurred while establishing the connection, or a network problem occurred."
The Cloud PC worked normally until it was handed off to another user. I later reprovisioned it back to my account, and the connection problem began. During that period, we also built out our CMMC enclave and applied policies and configurations to the device, although I had been using this Cloud PC throughout that work. The connection inspection reported no errors.
Where should I start troubleshooting this? Are there logs in Intune, Entra, Windows 365, or elsewhere that I can review without being able to sign in to the machine?
3 Answers
A recent Windows update can be another avenue to investigate, since some updates have caused RDP connection problems. However, I would check the Windows 365 service health, provisioning status, Intune policy results, Entra sign-in events, and Conditional Access evaluation first. Those sources should provide useful evidence even when you cannot access the guest OS.
The reprovisioning process is the biggest clue. Review the connection and provisioning history for that Cloud PC, then verify that the user is correctly licensed, assigned, and permitted to connect. If the service reports the device as healthy but the session still fails, ending any existing disconnected session or reprovisioning again may clear a stale session state.
Start with the Windows 365 Cloud PC status in Intune and the user’s Entra sign-in logs. Since the issue appeared after reprovisioning and policy changes, check for Conditional Access, configuration, compliance, or security policies that may be blocking session startup. Compare the current assignments with the configuration from when the Cloud PC was working.
There has been a long-standing RDP issue where disconnected sessions can become stale and refuse to reconnect until the session or machine is restarted. I have mostly seen that with standard desktops rather than Windows 365, but it is still worth checking for an orphaned session.