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Can someone tell me if I upgrade Windows Server with the trial iso and it works as a fit for me, will I be able to buy the license key and update, or will I have to reinstall again? TIA
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It isn't possible to perform an in-place upgrade using evaluation media.
--please don't forget to upvote and Accept as answer if the reply is helpful--
I didn't want to run the risk of doing it and then having to reinstall if it was not possible. I appreciate it.
It isn't clear now what you're asking? You can activate the evaluation to full if needed as long as it isn't a domain controller.
I am needing to upgrade my server and yes, it is a DC. I needed to make sure the hardware was smooth for Server 2016 from 2008 R2. If I install the eval version and it is good, it would have been nice to just upgrade the license.
Ok, I'd check here and with manufacturer about support for the hardware.
https://www.windowsservercatalog.com/
Then the prerequisite before introducing the first 2016 domain controller: domain functional level needs to be 2003 or higher
I'd use dcdiag / repadmin tools to verify health correcting all errors found before starting any operations. Then stand up the new 2016, patch it fully, license it, join existing domain, add active directory domain services, promote it also making it a GC (recommended), transfer FSMO roles over (optional), transfer pdc emulator role (optional), use dcdiag / repadmin tools to again verify health, when all is good you can decommission / demote old one.