In place upgrade of 2012 R2 server to either 2016 or 2019.

Cameron Watt 40 Reputation points
2023-10-25T20:28:27.5366667+00:00

I am trying to perform an in place upgrade on a server from 2012 R2 to 2016 or 2019, however, when I try either upgrade, the option to keep files and apps is greyed out. I have tried many fixes online but cannot find a solution.

It is an offline upgrade as the server in question is in an air gapped environment. I am trying to perform the upgrade using the eval ISOs from Microsoft. Is this the main issue? The server is licensed and activated. And if this is the issue, is the only way to successfully perform the upgrade by buying a Server 2016 or 19 license and using the ISO provided with the bought product?

Windows Server
Windows Server
A family of Microsoft server operating systems that support enterprise-level management, data storage, applications, and communications.
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  1. Dave Patrick 426.3K Reputation points MVP
    2023-10-25T20:53:40.4333333+00:00

    You'll need to use licensed installation media. An in-place upgrade using evaluation media is not possible to do. Even with licensed install media, depending on the roles or applications there could be other problems as well.

    --please don't forget to close up the thread here by marking answer if the reply is helpful--

    1 person found this answer helpful.

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