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I am running tests for the work related to upgrading the operating system while maintaining business apps intact. I'm facing troubles while doing the upgrade from Windows Server 2016 Evaluation Standard to Windows Server 2019 Evaluation Standard. I can do a clean upgrade, wiping out the personal files and apps, but I need to keep those files and apps.

However, I can't choose the second option. Only erasing all files is available. Same thing happens when I try to upgrade from Windows Server 2012 R2 to Server 2016 or 2019!

What might be the problem? Do I have to get a full licensed Windows to be able to do such an upgrade?

Any help or hints are appreciated .

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Dave M
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Alessandroesposito5
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    Consider the problem may be "evaluatoin". Why would upgrades be supported on an evaluation version. Test with a fully licensed version. – TomTom May 13 '22 at 09:33
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    Try the 2012 R2 Standard and 2016 Standard VL keys from here: https://docs.microsoft.com/en-us/windows-server/get-started/kms-client-activation-keys – Greg Askew May 13 '22 at 10:11

1 Answers1

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You can't upgrade to an evaluation edition. The article at the link below details your upgrade options. Although the wording isn't as clear as it should be, the following sentence spells it out:

Upgrades from a previous Windows Server installation to an evaluation copy of Windows Server are not supported.

https://docs.microsoft.com/en-us/windows-server/get-started/upgrade-conversion-options

joeqwerty
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