Upgrading Windows Server -Windows Cannot Find the Microsoft Software Licensing Terms

 

When attempting to upgrade from Server 2012R2 to 2016 or 2019 I received an error similar to this one. It may even say Windows 7 or Windows 10 going to a server version which makes you scratch your head.

Make sure you have a valid backup available if possible snapshot as needed

You can review the upgrade logs here:

https://support.microsoft.com/en-us/topic/log-files-that-are-created-when-you-upgrade-to-a-new-version-of-windows-9ec8aa31-0cc1-a0b2-2d98-e9c6714349b9

Make sure NO GPO’s are applying to the server that could impact licensing

If using KMS you can also drill down into its configuration but that’s a deeper dive than we needed:

https://learn.microsoft.com/en-us/windows-server/get-started/activation-troubleshoot-kms-general

Create a local Administrator instead of a domain Administrator

Install Windows Updates available and reboot

Disconnect from network

Attempt 1) Logon as local Administrator and attempt Upgrade

Attempt 2) Try removal from the domain temporarily and repeat reboot and upgrade attempt off network

Attempt 3)Open a CMD prompt and run the following and repeat reboot and upgrade attempt off network

 secedit /configure /cfg %windir%\inf\defltbase.inf /db defltbase.sdb /verbose

  

The above steps have permitted problem upgrades to complete 90% of the time

Don't forget to clean up your snapshots or rejoin to the domain after if necessary.

Note: If attempting to upgrade from Core to GUI you will have to convert from Core to GUI on the current OS first.  I have found that many of those fail and will not let you convert on the current OS. Post upgrade conversion from Core to GUI is a no go from my experience. In most cases a new server was built in the needed OS and applications/services transferred.  

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