I'm unable to connect to a Windows 365 Cloud PC. The client displays a black screen and then reports that the Remote Desktop Services session ended, possibly because an administrator ended it, an error occurred during connection setup, or a network problem occurred.
The Cloud PC worked previously, but after assigning it to another user and then reprovisioning it back to me, the problem returned. During that period, we also built out our CMMC environment and applied various policies and configurations. The Cloud PC was used throughout that work, so I'm unsure why the connection would behave differently now. The connection inspection completed without reporting any errors.
What should I check first, and where can I find useful logs if I cannot sign in to the Cloud PC?
3 Answers
There have been longstanding RDP issues where disconnected sessions become stale and refuse to reconnect until the session or machine is restarted. That is more commonly seen with regular desktop RDP than with Windows 365, but it is still worth checking for an orphaned session and terminating it or restarting the Cloud PC. Windows update history and recent session-related events are also useful places to look.
Because the machine worked before it was reassigned, compare what changed during reprovisioning rather than focusing only on the VM itself. Check the provisioning status, assignment, user licensing, and Windows 365 connection or session logs. If possible, reprovision it again with the expected policies excluded or applied in stages to identify whether a specific policy is responsible.
Start by checking the Entra sign-in logs and the Cloud PC status in Intune. Since the issue began after reprovisioning and policy changes, review Conditional Access, configuration profiles, security baselines, and any newly applied network or endpoint restrictions. A policy that blocks session initialization can produce this symptom even when the connection inspection looks healthy.
This behavior has been reported intermittently for many months with ordinary RDP sessions that remain disconnected for too long. I have not commonly seen it affect Windows 365, so I would investigate the provisioning and policy changes first, then treat a stale session as a secondary possibility.