An in-place upgrade using evaluation media is not possible to do. You'll need to use licensed installation media.
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Upgrading from Server Essentials 2016 eval to 2022 Essentials eval
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CIT0440
51
Reputation points
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?
Windows for business | Windows Server | Devices and deployment | Set up, install, or upgrade
Windows for business | Windows Server | User experience | Other
Answer accepted by question author
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![](data:image/svg+xml, %3Csvg xmlns='http://www.w3.org/2000/svg' height='64' class='font-weight-bold' style='font: 600 30.11764705882353px "SegoeUI", Arial' width='64'%3E%3Ccircle fill='hsl(128, 8%, 22%)' cx='32' cy='32' r='32' /%3E%3Ctext x='50%25' y='55%25' dominant-baseline='middle' text-anchor='middle' fill='%23FFF' %3EA%3C/text%3E%3C/svg%3E)
Anonymous2023-12-10T00:05:36.0933333+00:00 -
CIT0440 51 Reputation points
2023-12-10T00:10:14.66+00:00 If licensed media is used to test, won't that affect activation of production server?
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Anonymous
2023-12-10T00:22:35.5166667+00:00 No, you can install the server but just skip activation for time being.
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CIT0440 51 Reputation points
2023-12-10T00:33:19.7266667+00:00 Awesome... Thanks!
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Anonymous
2023-12-10T00:35:08.0933333+00:00 You're quite welcome.
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abbodi86 4,851 Reputation points2023-12-10T15:26:05.17+00:00 Server 2022 Essentials edition/media does not exist, you are trying to upgrade Essentials to Standard, hence no full upgrade option