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JoelLevine-9365 asked JoelLevine-9365 commented

Server 2016 upgrade to 2019 won't allow me to keep existing setting and apps

I can't upgrade an existing Server 2016 to Server 2019 and keep my existing apps and settings, it is grayed out. This is a Volume Licensed product, fully updated and I am using the latest ISO that could be downloaded. This is occurring on multiple machines so its not a quirk on just one of them.

windows-server-2016
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TeemoTang-MSFT answered JoelLevine-9365 commented

The most common cause for this “can’t keep files and settings” issue is system language mismatch.
Check the target ISO language and current system language, if the Target language is not compatible with current language, in-place upgrade can’t keep existing apps and settings.
You could check the setupact.log for related information.


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Thank you for the response, I have ensured that there is no language mismatch as both versions are configured for English. I did look at the set-up log but nothing is standing out as a possible cause, I will continue to hope that someone else has experienced this problem.

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Ok, let's wait for others ideas.
If further assistance were needed you could open a request ticket with Microsoft support.
https://support.serviceshub.microsoft.com/supportforbusiness

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Thank you, I may but want to give this another day or two.

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