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r/sysadmin • … • u/hoagie_tech

Do you need to do Windows Update before in-place upgrade of Windows Server OS?

I'm not finding a definitive answer to this question: If I have a server that does NOT have the latest Windows Updates available for that OS installed, is it okay to skip the updates and just run with the in-place upgrade?

For example a 2012R2 server that does not have the October 2023 Cumulative update waiting to download/install. Can I just start with the 2019 in place upgrade or should I do all updates first?

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