Bought licenses for Windows server 2019 because Microsoft documentation claims you can upgrade from Windows Server 2012 R2 directly in-place. Please note, this IS what we need to do so discussions about "best practices" and VMs and migrations are not helpful for this particular occasion. I will be guiding us toward that later, but baby steps for now.
Microsoft only allows the download of the EVAL version. When I run this on our server to install, the "upgrade" option aka "Keep Files…" is disabled. It only gives me the one choice of "wipe it all out and start over" which is not what the documentation from Microsoft claims.
The authorized reseller who we bought the codes from only links to a very detailed document on upgrading and downloading the EVAL ISO from MS.
Microsoft is a minefield of getting someone to talk to. We just spent a ton on their software and getting someone to answer questions without a paid support contract is nearly impossible. I understand and support paid support down the road, but not when their software is not working as they promise it will. Google is not your friend here either as most questions come back to "how to upgrade the eval to full version" which is well after the point I'm at for installation.
Has anyone successfully directly upgraded IN-PLACE Windows Server 2012 R2 to 2019?
If so, was there anything special you had to do?
If not, will it work to go to 2016 first and then to 2019?
(Just tried 2016 and the in-place option is also disabled)
Best Answer
You can upgrade in-place, but not to an evaluation edition.
This isn't Microsoft's fault. They clearly state that upgrading to an evaluation version isn't supported. It's working exactly as it's intended. - https://docs.microsoft.com/en-us/windows-server/get-started/supported-upgrade-paths
Yes, if you're evaluating it. You purchased it. You need to get the installation ISO from the Volume License Service Center. Your order should include an authorization number and you should have received an email from the VLSC prompting you to login or create a login to access your product and keys. If you didn't then I'd ask the authorized reseller why you didn't.