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Is there a way to upgrade from windows server 2016 standard license ( no EVALUATION) to windows server 2019 using ISO method without the need to activate it in a second moment once the upgrade is over?

During the Upgrade/Installation Wizard, no prompt for a license key is shown !! and if I go further, I'm not able to keep my files/apps and the only option is to do a clean installation/upgrade. And I need to keep the previous installation !!

Both windows servers 2016-2019 got a license key.

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3 Answers 3

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what you are looking for should be described in the link on the Microsoft website:

https://docs.microsoft.com/en-us/windows-server/get-started/upgrade-2016-to-2019

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  • Please provide the relevant steps from the link to resolve the problem.
    – Paul
    May 18, 2022 at 13:14
  • Thank you for your reply ! Where can I find a Windows server media non Evaluation version ?
    – Alessandroesposito5
    May 19, 2022 at 10:34
  • You can use the Evaluation media, and you can change the version from PowerShell using following command and setting the License Key: DISM /online /Set-Edition:ServerStandard /ProductKey:XXXXX-XXXXX-XXXXX-XXXXX-XXXXX /AcceptEula I suggest however to do a full raw copy of the whole disk to be safe and avoid surprises, before any upgrade.
    – Massimiliano Catinoto
    May 19, 2022 at 18:02
  • I'm already aware of this option , What I need is to do the update of the Operating System (wile keeping the files/apps to test the integrity of the already installed app/configurations on the new S.O) . I don't need to do a clean upgrade and reinstalling the previous apps/configurations ! What I'm looking for is a licensed installaion media (ISO) and not an Evaluation version ( Having already the license key to insert during the upgrade process ) Thank you for sharing , much appreciated.
    – Alessandroesposito5
    May 20, 2022 at 10:00
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You can't use the Evaluation-ISO to upgrade. Did you buy a retail copy with DVD included? Otherwise you could grab one from MSDN, if you have an active subscription.

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I had the same issue and I resolved it by mounting the ISO and changing the edition.

After copying the ISO files to a folder I ran the following:

dism /mount-wim /wimfile:c:\ISO\sources\install.wim /mountdir:c:\mount /index:2

dism /image:c:\mount /get-currentedition

dism /image:c:\mount /get-targeteditions

dism /image:c:\mount /set-edition:ServerStandard

dism /unmount-wim /mountdir:c:\mount /commit

Then I ran the setup file and it still listed eval under the options, but then it allowed me to choose to keep my files.

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