You can and should install evaluation versions as clean installs. There's no support for upgrading from a previous Windows Server installation to an evaluation copy.
You can't downgrade from Standard back to Eval. There's no support for converting the Core edition to Server with the UI, even though some sources have been saying Microsoft will finally implement this in WS 2019. You should follow the usual Microsoft checklist concerning DCs before the upgrade. If you have a domain controller (DC), you'll need to run a Forestprep and Domainprep prior to the upgrade. You can then change the language UI only. You'll have to upgrade to the same language. There's no support for upgrading from one language to another. Here are a couple of known facts about upgrading from a previous release of Windows Server (WS 2012 or WS 2016): But you need to be aware of some considerations first. If you think that upgrading between server versions is easy, it might be in some situations. There are situations when an upgrade won't work. There's support for some use cases but not others. It is possible to activate the evaluation versions.The possibility of converting a Microsoft OS isn't new, but previously, back in the day, this was not really possible.Īlthough in this post we'll focus only on converting licenses or editions, you might be looking also for upgrade options. 
The evaluation versions of Windows Server 2019 are the same as the paid retail versions.
Windows Server 2019 Features on Demand (FOD) - for Server Core only Windows Server 2019 Datacenter with Desktop Experience (.VHD) ISO - This ISO contains both versions of installation i.e. Windows Server 2019 Standard or Datacenter. I figured I would dump the direct links here for my future use, and for anyone else if they are in the same predicament.ĭirect Download Links for 180-Day Evaluation I have uploaded the SxS folder to my GSuite Drive account, you can download just that folder below: NET Framework 2.0 (Don't ask), so after some searching I found the direct links to the Windows Server 2019 ISO files hosted on Microsoft's servers. I needed to source the SxS folder to install.
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