Hey everyone! I'm in a bit of a bind here with one of my Azure VMs running Windows Server 2016. We've got an RDS farm, and all our servers handled the latest updates just fine—except for the RDS Broker. This server is stuck in an endless reboot loop after trying to install the September updates, specifically: the Servicing Stack Update (KB5065687), a .NET Framework update (KB5065749), and a cumulative update for Windows Server (KB5065427). I've rolled it back to a previous backup, but as soon as I try to install the updates again, the issue pops back up. Unfortunately, we can't access the logs since we don't have Bastion set up to connect remotely during boot. I was considering changing the VM size from a B-series to a D-series, but I'm not sure that would help. If anyone has any ideas on what I can try, I'd greatly appreciate it! Thanks!
4 Answers
I get it, running 2016 still is a bit of a gray area! But hey, it doesn't hit EOL until January 2027. Have you considered restoring your VM to a different environment and applying updates there first? That way you won't risk your production environment while troubleshooting. Testing them one at a time could also help pinpoint which update is causing the headache.
Exactly! With how long updates take on 2016, it's wise to avoid unnecessary downtime. You’re not alone in this; others are in the same boat.
If you can manage to get it to stop rebooting, try manually extracting the update files and installing them using DISM. Start with the SSU and then move to the cumulative update, but make sure to reboot between each patch. For extracting, use something like `expand -F:* C:pathtoupdate.msu /F:* C:destinationfolder`. That way, you can see where things go wrong without having it boot automatically.
Hey! I had a similar experience. I managed to boot my server by selecting "Disable driver verification" from the F8 menu. Once I got in, it completed the update successfully—maybe worth trying if you can get to that screen!
Have you tried booting into Safe Mode and running some basic DISM commands? You might want to start with: `dism /online /cleanup-image /startcomponentcleanup /resetbase`. Also, check the logs at `windowslogscbs` and `dismlog`. If it gets stuck, you might need to terminate a few processes, like `dism.exe` or `tiworker.exe`, and see if that releases the hold-up.
Thanks for the tip! I'll definitely give that a shot. It sounds like a good way to troubleshoot this mess.
Yes! Sometimes those commands can clear out a lot of issues. Good luck!

Good point! EOL is still a while off. Just take it one step at a time.