Strange behavior of Windows Server 2019 Essentials in licensing

Question

Hi.

I am an IT technician. English is not my native language, so I am sorry for any bad syntax.

To begin with, a client of mine has bought a new Dell PowerEdge Server for its company, to migrate someday its data and services (mostly file sharing inside the company through LAN) from the old server machine with Windows Server 2008 R2 on it.

So, the newly purchased Dell Server came with no OS installed. Therefore, I downloaded a 180-days trial version of Windows Server 2019 Essentials from Microsoft’s web site and I installed it to it.

Then, after some days (and after successful installation, updates, drivers, etc.) I run some programs on this system (mostly for files backup) to be sure as far as concern compatibility of these programs with 2019. Then, for some months (about 3-4 months) the server worked fine with the trial version installed. At about the 4th-5th month my client powered it off due to a problem with the room temperature and air-conditioning. The server was switched-off all the time, until 3 days ago (that is, 6-7 months after the initial installation of Windows).

So, before 3 days I switched it back on and Windows told me that there were updates. I did all updates and after 2-3 restarts the license changed by its own and became Windows Server 2019 Standard Evaluation!

My client meanwhile bought a Windows Server 2019 Essentials license and when I tried to put this Product Key for activation, the activation gives me instantly an error and the Windows cannot be licensing!

Why Windows became automatically from Essentials, a Standard version?

Is it a common situation?

How can I roll-back to Essentials and to activate the newly purchased license?

Thank you.

Answer 1

@Dave Patrick

you will be greeted with message Windows License is expired and your Windows Server machine will start shutting down.

Well, that's the problem!

Why this does not happened to my client?

Instead of this, Windows became Standard edition evaluation and continues to work fine!

The problem here is that (if you are true) I must formatting the Server and to Clean install Windows again plus drivers plus programs plus roles plus setting plus files plus etc... This is a real pain for me plus for my client!

Is this a BUG?

@UdaraPeiris-2218 I read the PDF, it tells me only about the downgrade rights, not the way to do it! Do you have more information about the downgrade procedure without to loose any settings / files / installations etc. ?

Answer 2

Something here may help. Stand up a new one and do the migration.
https://learn.microsoft.com/en-us/windows-server-essentials/migrate/migrate-from-previous-versions-to-windows-server-essentials-or-windows-server-essentials-experience

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