Remote Desktop fails without error message

Solution 1:

Verify that it actually rebooted - if you can do a "net use" against the remote server, then connect to Event Viewer to see if it actually did reboot. I've seen plenty of Win2k3 servers that, when rebooted from an RDP session, don't actually reboot but stop responding to RDP. If that's the case, you can do a shutdown /i against the server or use some other out-of-band method of actually executing the reboot.

And if this is the case, in the future, don't reboot from a regular RDP session. Reboot only from the /console or /admin connection, or use shutdown /i, or other remote methods.

Solution 2:

After further investigation of the event log, I think I have found the problem. There was this error almost exactly after the restart was initiated:

The Windows Modules Installer service did not shut down properly after receiving a preshutdown control.

So the problem was that some the services were shut down, while this particular service was hanging. It seems to have been killed after a timeout occurred (one hour), after which windows has rebooted as intended.

Now the only remaining question is how to prevent this in the future. Obviously I'd like future reboots to run a bit faster than this...

Solution 3:

I had a problem using remote desktop on a server 2003. I connected and after seeing some status messages I was disconnected before seeing the full desktop.

The Problem was, that the server had a wrong time because the synchronization failed for a few month (I think there was a time difference of about 30 minutes).

Solution 4:

I got here through Google with the same problem with my Windows Server 2012 (7 years later), so I'll add my own experience with the problem for future searchers. Here's what happened:

1. In light of the recent WannaCrypt attacks, I installed all pending security updates from Microsoft. Naturally, a reboot was required. For the second time. In less than 24 hours. On a server which was running for 350 days straight before this whole mess. I hope all hackers burn and rot in hell (I'm an atheist BTW, I don't even believe in hell).
2. I clicked the restart button in Windows Update. My RD session was terminated immediately and all attempts to reconnect would fail with no error message, but the server was still up and running uninterrupted and serving pages. I know this because my AppPool takes one or two minutes to fully load each time it's taken down. I'm guessing that Windows Update was going through some preliminary steps which didn't require other services on the system to be shut down.
3. After a few more (very long and stressful) minutes, the server would return HTTP 503 for all requests. I could still ping the server though. Guess: server still running, IIS shut down, more serious update work in progress.
4. A minute or so later, I lost all access to the server. No kernel, no Windows, nothing, waiting for the system to come back online after the actual reboot.
5. After another minute, the ping was back, and I actually managed to connect to RD in time to see the final steps of the update being applied. Server is running normally since.

So, if you lose remote access to your server immediately after reboot, don't panic, it's probably doing some maintenance work and will come right back online after it's done.