Problems updating 2016 to 2019

Jeffrey Pascone 21 Reputation points
2020-09-09T17:47:00.16+00:00

I have a 2016 server I am trying to update to 2019.

At the "choose what to keep" screen "keep personal files and apps" is grayed out making "Nothing" the only selectable option.

I very much need to migrate my apps and settings. I have tried booting to the ISO as well as running it after the server is up.

23476-2020-09-09-13-35-17-hacwdcapp231-remote-desktop-co.png

Windows Server
Windows Server
A family of Microsoft server operating systems that support enterprise-level management, data storage, applications, and communications.
12,170 questions
Windows Server Migration
Windows Server Migration
Windows Server: A family of Microsoft server operating systems that support enterprise-level management, data storage, applications, and communications.Migration: The process of making existing applications and data work on a different computer or operating system.
408 questions
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Accepted answer
  1. Dave Patrick 426.1K Reputation points MVP
    2020-09-09T17:50:33.947+00:00

    An in-place upgrade is never recommended. Better option is to clean install Server 2019 and migrate the roles or applications over to it. That being said you can run setup.exe from the root of the licensed install media to start the upgrade.

    --please don't forget to Accept as answer if the reply is helpful--

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  1. Teemo Tang 11,341 Reputation points
    2020-09-10T02:12:01.32+00:00

    Look at the explanation sentence on the bottom:
    Your files apps and settings can't be kept because you're installing an edition of windows that's different than the one you’re currently using.
    This sentence usually has two meanings:

    1. You need to use licensed media to perform an in-place upgrade. Evaluation media cannot be used.
    2. You need to check the base OS language matches between 2016 and 2019.
      In fact, just as DSPatrick said, in-place upgrade server is never a recommended behavior, Windows 10/Server 2016 'upgrade' processes are essentially a clean-install, and then migrate data.

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