Hello @Derek Benak ,
1.The Session Host server logs a warning when the grace period is about to expire. At the end of the grace period, if there is not a license server present with valid RDS CALs installed, users will no longer be able to establish RDP sessions on the RD Session Host server. So it will be necessary to ensure that it is configured to connect to a valid RD license server and that the appropriate RDS CALs have been purchased and installed.
https://social.technet.microsoft.com/Forums/windowsserver/en-US/17b1582e-16fd-4e08-8d1f-a4ab4623ba60/what-happens-when-the-rds-licensing-grace-period-during-which-no-license-server-is-required?forum=ws2016
2.Did you activate the Remote Desktop Services license server and install RDS client access licenses on the Remote Desktop license server?
https://learn.microsoft.com/en-us/windows-server/remote/remote-desktop-services/rds-activate-license-server
https://learn.microsoft.com/en-us/windows-server/remote/remote-desktop-services/rds-install-cals
3.The following document will give you better understanding on how RD Licensing role works.
https://nedimmehic.org/2018/04/16/remote-desktop-services-2016-licensing/
Please Note: Since the web site is not hosted by Microsoft, the link may change without notice. Microsoft does not guarantee the accuracy of this information.
Best regards,
Leila
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