Hey everyone!
I know, I know, I probably shouldn't be using Windows Server 2016 anymore, but I'm dealing with it for now. I have an RDS farm in Azure, and all of our servers handled the last round of updates without any issues—except for our RDS Broker. It has been stuck in this annoying reboot loop. We rolled it back to an earlier backup, but when we tried the updates again, surprise, the problem came back. I can't seem to find any solutions online, so I'm turning to you all for advice. Unfortunately, I can't access the logs since we don't have Bastion set up, which means I can't connect when it's booting up.
The problematic updates are:
- 2025-09 Servicing Stack Update for Windows Server 2016 (KB5065687)
- 2025-09 Cumulative Update for .NET Framework 4.8 (KB5065749)
- 2025-09 Cumulative Update for Windows Server 2016 (KB5065427)
I was thinking about changing the VM hardware from a Bseries to a Dseries, but I'm not sure that would help. I really need some guidance here. Thanks!
1 Answer
It sounds like you’re dealing with a problematic update. A good approach is to try installing the updates one by one to see which one causes the issue. You mentioned the server worked fine with other updates—so it could be one of them causing the trouble for this specific VM. Also, changing the VM SKU probably won’t help in this case.
Yeah, it’s definitely strange how it’s just one server having issues when the others are fine. As for installing updates individually, unfortunately, it’s not a straightforward task, but you could maybe create a snapshot and try applying updates one at a time.