An in-place upgrade using evaluation media is not possible to do. You'll need to use licensed installation media.
--please don't forget to close up the thread here by marking answer if the reply is helpful--
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I have several clients running Windows Server 2016 Essentials and am planning in-place upgrades to Windows Server 2022 Standard. I would like to perform a test upgrade prior to production. I installed and configured an evaluation version of Windows Server 2016 Essentials on a test server. When I run the Windows Server 2022 upgrade, my only option is a fresh install. The option for keeping files, settings and applications is greyed out. Is this because these are evaluation licenses?
An in-place upgrade using evaluation media is not possible to do. You'll need to use licensed installation media.
--please don't forget to close up the thread here by marking answer if the reply is helpful--
Server 2022 Essentials edition/media does not exist, you are trying to upgrade Essentials to Standard, hence no full upgrade option