I'm looking for advice on upgrading our RD gateway servers from Windows Server 2016 to Server 2022. We have several production and non-production servers that currently serve as RD gateways in AWS, and they're set up in pairs behind a load balancer to share the workload. These servers are regularly patched and have been performing reliably. Since our company plans to phase out Windows Server 2016 in the next 9-10 months, we need to upgrade to Windows Server 2022. I'm particularly interested in any concerns regarding (1) doing an in-place upgrade of these servers, and (2) the overall stability of the RD gateway services on Windows Server 2022. I've participated in in-place upgrades before, but I've never managed RD gateway upgrades specifically. I'd appreciate any guidance or insights based on your experiences!
5 Answers
Honestly, it might be quicker and less risky to just set up a new RD gateway instead of upgrading in-place. I can usually get a new one running in under an hour, so you could save yourself some headaches that way!
I'd advise treating this upgrade as if you were setting up brand new RD gateways. Instead of an in-place upgrade, consider doing a blue/green deployment. RD Gateway usually functions fine through upgrades, but there can be subtle issues that only show up under load, like with NPS or cert bindings. Setting up parallel 2022 instances behind your load balancer sounds like a smart approach. Just ensure everything is tested thoroughly before cutting over fully!
If you're concerned about potential issues, I'd recommend checking out Microsoft's documentation on upgrading RD services. They usually highlight the common pitfalls you might encounter. Here's a link to their guidance: [Microsoft Docs](https://learn.microsoft.com/en-us/windows-server/remote/remote-desktop-services/upgrade-to-rds). It should help you navigate the upgrade smoothly!
I remember running into issues with settings not transferring correctly during my upgrade. Make sure to back everything up just in case, and you might need to use a PowerShell script to re-import your configurations after the upgrade. It can save a lot of time!
In my experience, I've done in-place upgrades without much hassle, except for dealing with the Network Policy Server (NPS). When that happened, I just switched to local NPS during the upgrade and switched back afterward without any problems!
Yeah, their docs are pretty solid for understanding what might break. It's worth a read!