Upgrade Fresh Factory Installed Windows Server 2016 to Windows Server 2019

Purchased a dell poweredge server last year but due to some reason beyond our control we could not set it up. We however unboxed it a few days ago and powered it up. The system came with factory installed windows server 2016 as we specified Dell to do with its license of a Windows Server® 2016,Standard Ed, 16CORE License plus additional 12 CORE License because it has dual CPU of 14 Core each. As I write the system is clean install and we have not installed any server role service on it. We however want to upgrade it to Windows Server 2019 before we install Active Directory and the rest. Please help us by showing us the way we can go about that and whether we can do it like how we upgrade our windows 8.1 computers to windows 10 using the windows media creation tool, where needed not to put in any new key but they inherited that of the pre-existing key of windows 8.1 pro.
Can we install or upgrade to Windows Server 2019 Standard Edition using the keys of the Windows Server® 2016,Standard Edition.

There is no legal way to upgrade from Server 2016 to Server 2019 in the same way you could from Windows 8 to Windows 10, unless you have some form of Microsoft Volume License subscription. The Windows 7/8 to 10 free upgrade was a onetime offer from Microsoft to push everyone to Windows 10 as it makes things easier for them and makes the installation statistics look better. If you purchased the server with the OS installed you almost certainly purchased it with an OEM copy of the OS. Therefore the license is tied to that hardware and dies with that hardware, and you have to buy a copy of Server 2019 if you want to upgrade.

If you are asking how to install a copy of Server 2019 you have purchased without wiping it then you would do an in-place upgrade. Although there would be no point doing that if it’s a clean system as a clean install would be quicker and less prone to issues down the line.

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@Acestes So what is your advice then, will I have to continue with the Windows Server 2016 because spent a lot purchasing that license. Is it ok to go with that version or it has problems than the Windows Server 2019

I can’t tell you what to do as I don’t know your environment or your budget. However, Server 2019 isn’t that different to Server 2016 (I run several 2016 servers in production), so unless you need a specific feature that is in Server 2019 I would stick with what you have. Server 2016 extended support ends in 2027, so you have a good few years to use it.

@Acestes Alright thanks for your help :+1: