The Windows September Update is causing a lot of headaches for system administrators, by the looks of it break the functioning of remote desktop services on Windows Server 2019, 2022 and 2025. This prevents you from connecting to machines remotely and sometimes requires a forced reboot before you can connect again.
Remote Desktop not working on Windows Server due to updates
The September cumulative update of Windows Server is causing quite a few headaches for system administrators due to the fact that it would make connections via RDP (Remote Desktop Protocol) impossible. Symptoms reported by some users on Reddit include connections stuck at “connecting…” and never reaching the login screen, users already on the system unable to log out, Task Manager crashing when opened, event 6005 being logged in the system logs, and a normal reboot stalling.
The problems would recur a few hours after the forced reboot, and would disappear once the update was uninstalled. According to what a user writes on Reddit, the cause of the problem is that a deadlockwhich is a situation where two parts of the system wait for each other resulting in a hang, when a connection is closed.
Microsoft has not confirmed the problems, nor their cause. The company is reportedly investigating the situation, as reported BleepingComputerand said it will release additional information as it becomes available. Ironically, this issue comes after the company publicly pledged to improve the quality of Windows after the operating system saw widespread discontent as patches constantly introduced new problems.
