I have 2 machines with one [Server 2019 Standard] acting as a licensing server for my non-domain workgroup and the other a 2016 Standard machine. I configured the licensing server on the same day for both machines.
I installed the remote desktop licensing service on 18-Mar-2020 and installed 50 user and 50 device licenses. original install date for the machine running the licensing service is Feb-2019
I was then able to connect with 10+ clients on either machine simultaneously.
Today, 27 days later, connecting clients on the machine which hosts the licensing server receive: "there is a problem with your remote desktop license and your session will be disconnected in 60 min"
This error does not appear when connecting to the other machine.
I have 7 sessions from a single laptop between both machines. The RD Licensing Manager shows "issued" as 0 for both device and user CALs.
I read that workgroup machines don't allow user CALs, so I converted mine to device CALs. Still 0 issued.
I verified that the local gp on either machine was configured [comp config > admin templates > rds > rd licensing > remote desktop session host > licensing >
1] use specified server is configured on both servers 2] remote desktop licensing mode was user, now set to device
used gpupdate /force when making changes, but the message about the 60m timeout persists on connection
RD licensing diagnoser "did not identify any problems to report"
i rebuilt the licensing database and re-applied the per-device licenses with no effect.
tried deleting MSLicensing registry key with no effect.
there are certificate entries in:
Computer\HKEY_LOCAL_MACHINE\SYSTEM\CurrentControlSet\Control\Terminal Server\RCM
...but I have not touched them
edit: I noticed that the license diagnoser on the 2019 machine is showing the version of the license server configuration is "Windows Server 2016" even though it is running on Windows Server 2019.
I also installed device licenses for 2016 as well, but this did not help.