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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)

WoJ
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klkitchens
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    On Stack Exchange sites, marking an answer "accepted" is the proper way to indicate that your problem has been solved. They're Q&A sites, not forums, so don't put "solved" in the title or edit comments into the top of the question (if you are clarifying, it's fine to edit them into the bottom). – chrylis -cautiouslyoptimistic- Nov 23 '21 at 02:05

3 Answers3

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Bought licenses for Windows server 2019 because Microsoft documentation claims you can upgrade from Windows Server 2012 R2 directly in-place.

You can upgrade in-place, but not to an evaluation edition.

I understand and support paid support down the road, but not when their software is not working as they promise it will.

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

Microsoft only allows download of the EVAL version.

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.

joeqwerty
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    That literally is it. Licenses bought = download. And the VLSC is the place things are handled these days. – TomTom Nov 22 '21 at 17:36
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    Thanks @JoeQwerty. This is the first I've been told you cannot upgrade to the EVAL download, so thank you for that. You'd think the Authorized Reseller would know this and NOT indicate to download the Eval ISO in the directions specifically sent by them for upgrading a server. Will try to track down the ISO. – klkitchens Nov 22 '21 at 19:01
  • Glad to help... – joeqwerty Nov 22 '21 at 20:29
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  1. Server 2012 R2 upgrade to 2019 is supported

  2. Upgrading to evaluation version is not supported. You should obtain non-eval installation media to upgrade your server. The location of the media depends on your licensing program type. If you purchased via Volume Licensing, you might have a media located at business portal

Or just find Windows Server 2019 ISO... somewhere

Hope this helps

J-M
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    Thank you very much. I'm shocked MS doesn't make the server ISO available like they used to, but only the evaluation version. I 'found' one elsewhere, but it was core only and need the desktop experience for this server (and core for soon to be VMs)... thanks so much We did not get the VL invite that I can find, but will check some more. – klkitchens Nov 22 '21 at 18:58
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The Evaluation version is not supported to do the in place upgrade, you need to use the retail version and follow the steps https://docs.microsoft.com/en-us/windows-server/get-started/upgrade-2012r2-to-2019 and I get the retail version download and Server 2019 datacenter Product Key from the microsoft online partner store keyingo.com, they also give me the instruction above and I successfully upgrade from server 2012 R2

davida wright
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