So far, this is my only hiccup with Server 2019. After running the above commands, my servers were activated and running normally. Some users reported completely reloading Windows and entering the key from the start to resolve the issue, but if you have already configured the server or workstation, that’s not really an option.
Lastly, activate Windows by entering the command slmgr.vbs /atoįrom my research, this appears to be a fairly common issue. 
To enter your new product key, use the command: slmgr.vbs /ipk xxxxx-xxxxx-xxxxx-xxxxx where the x’s are your actual product key. Clear the product key from registry by running slmgr.vbs /cpky. To remove any existing product key (in case you used a trial key), enter and run the command slmgr.vbs /upk. Right Click and choose Run as administrator. Click Start and type CMD in the Start Search menu. In this article, I will show you how to enter your product key manually using command line utilities, then activating using the same utility. The window did not pop up, no error in the event logs, nothing at all. Once the licensing arrives, you can enter the product key from the Settings app, but in my case, clicking the Change Product Key button resulted in absolutely nothing. When installing Windows Server 2019, as with previous versions of Windows, you are prompted to enter the product key during installation, however if you are waiting for licensing to arrive, you can skip this and continue building your server.
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