Problem upgrading Server 2012 R2 to 2019

Eric Keil 10 Reputation points
2023-01-20T01:16:54.8433333+00:00

Evening All, I have run into an issue I don't know if there is a fix for. I am hoping someone here can assist.

I am doing an upgrade of a server running Windows Server 2012 R2. When this server was first purchased many years ago it had Windows Server 2012 R2 Essentials on it. As the business grew we had to upgrade that server from Essentials to Standard.

Now when I go to do an in-place upgrade of the server it will not allow me to upgrade the apps and settings. It wants to wipe everything out. I have upgraded Server 2012 R2 Standard to Server 2019 Standard about 5 times without issue. So I know the upgrade path is ok. I think because the server used to be Essentials edition it will not let me do it. I have completely removed the Essentials Experience from "Remove Features" in the Dashboard. I have combed through everything and I do not see anything left from the Essentials edition.

Please let me know if you have any ideas.

Thank you,

Eric

Windows Server 2019
Windows Server 2019
A Microsoft server operating system that supports enterprise-level management updated to data storage.
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Windows Server 2012
Windows Server 2012
A Microsoft server operating system that supports enterprise-level management, data storage, applications, and communications.
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A family of Microsoft server operating systems that support enterprise-level management, data storage, applications, and communications.
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  1. Eric Keil 10 Reputation points
    2023-01-20T01:52:52.71+00:00

    Found the issue. Stupid on my part. I was not using the correct iso file. I was trying to upgrade to Server 2019 Standard (Non Desktop Experience). With the correct ISO I selected the Desktop Experience version and everything is ok now.

    2 people found this answer helpful.

  2. Limitless Technology 44,551 Reputation points
    2023-01-20T17:06:19.1533333+00:00

    Hello,

    This is correct, the only continuous upgrade path for Essentials would be newer edition of Essentials, such as 2012R2>2016>2019.

    If you perform a version upgrade from Essentials to Standard, the new Standard version will not allow the upgrade to newer Standard versions.

    --If the reply is helpful, please Upvote and Accept as answer--

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