I'm currently managing two Remote Desktop Services (RDS) licensing hosts in Azure running Windows Server 2022. While I've had no trouble issuing per CAL licenses for both Windows Server 2019 and 2022, I'm running into problems with licensing for Windows Server 2016—it just doesn't seem to work. I've already checked a few things and would appreciate any advice on further steps I might take:
1. My session hosts are configured to point to the right license servers, and they can communicate without issues. They've also been set up for per CAL licensing.
2. The licensing hosts are activated, and I've verified that the time settings are consistent between the session host and the license servers.
3. I attempted to run lsdiag.msc from System32, but I noticed that this tool isn't available on the license servers.
4. I executed a PowerShell command to install the necessary RDS licensing features, but it didn't resolve my problem.
5. I used the Get-WindowsFeature command to check the status of related components, and both Remote Desktop Licensing and the management tools are installed.
6. When I ran the install command again, it indicated no changes were needed, so I'm at a loss for how to proceed with fixing the licensing for Server 2016. Any insights would be greatly appreciated!
1 Answer
One quick fix could be to upgrade your Windows Server 2016 machines. It might seem like a hassle, but getting them on a newer version could resolve the licensing issues you’re facing now. Just something to consider!

I hear you, and it's on my list for the next few months! But right now, I really need to sort out this licensing issue.