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Windows compatibility is insane!
(lemmy.ml)
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this post was submitted on 21 Jun 2023
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Microsoft has not been providing public updates for that platform for years, it needs to be retired. If it's a VM, take a snapshot and do an in-place upgrade, see what happens. Revert to snapshot if it doesn't work out.
https://learn.microsoft.com/en-us/lifecycle/products/windows-server-2008-r2