Unable to upgrade Server 2019 Essentials to 2019 Standard

Question

I have several Server 2019 Essentials servers that are licensed with a VLSC Key. I am trying to upgrade to Standard edition with valid VLSC keys for this product, by using DISM command. I am getting the following error on all the servers:

DISM.exe /Online /Set-Edition:ServerStandard /ProductKey:XXXXX-XXXXX-XXXXX-XXXXX-XXXXX /AcceptEULA
Error: 1168, The specified product key could not be validated.
Check that the specified product key is valid and that it matches the target edition.

I checked they can be upgraded:

DISM /Online /Get-TargetEditions
Editions that can be upgraded to:
Target Edition : ServerStandard

The ISO image used to install 2019 Essentials was downloaded from the VLSC site, so there should not be any version issues relating to Volume Licence vs OEM installs.

Microsoft telephonic support suggested re-installing, which is not an option since the servers are in production use.

Can anyone shed some light on how to resolve this without trashing the OS.

Answer 1

Hi,
Have you tried the method of KMS key instructed in below post?

Dism /online /Set-Edition:ServerStandard /AcceptEula /ProductKey:N69G4-B89J2-4G8F4-WWYCC-J464C

then after conversion (using your new key);

slmgr /ipk xxxxx-xxxxx-xxxxx-xxxxx-xxxxx

slmgr /ato

Reference links:
KMS client setup keys
https://learn.microsoft.com/en-us/windows-server/get-started/kmsclientkeys
Upgrade Server 2019 Essentials to Standard - specified product key could not be validated
https://social.technet.microsoft.com/Forums/security/en-US/debc3002-3846-4876-a401-fbf2a2a71519/upgrade-server-2019-essentials-to-standard-specified-product-key-could-not-be-validated?forum=winserversetup

Error 1168 – The specified product key could not be validated.
https://doitfixit.com/blog/2019/10/09/error-1168-the-specified-product-key-could-not-be-validated/

Please note: Information posted in the given link is hosted by a third party. Microsoft does not guarantee the accuracy and effectiveness of information.

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Hope this helps and please help to accept as Answer if the response is useful.

Thanks,
Jenny

Answer 2

Thank you for this solution, Jenny

Worked like a charm on one of the servers so far.

The conversion removes and reconfigures components. I have 2x AD controllers that also need to be converted.
Do you know if the AD configuration remains intact after conversion?

Thanks,
Sasha