Is it possible to upgrade from Windows Server 2008 R2 to 2025 using an evaluation version of 2012?

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Asked By CleverFox123 On

I messed up and didn't check the upgrade paths for my Windows Server versions. I have fully licensed copies of both 2008 R2 and 2025. I'm wondering if I can use an evaluation version of Server 2012 to go through the upgrade process correctly? My plan is: 1) Join the 2012 evaluation to the domain and promote it to PDC. 2) Remove the 2008 AD DS role and turn it off. 3) Then join the 2025 server to the domain and promote it to PDC. 4) Finally, I'll remove the 2012 role and turn it off. Will this work? Am I missing anything?

2 Answers

Answered By TimeTravellingAdmin On

Honestly, if you're this far out of date, you might as well consider starting fresh. Go back to 2020, upgrade from 2008 R2 before EOL, then jump ahead to 2023 for 2012. From there, you can continue hopping to newer versions before they hit EOL. Carrying over two decades of legacy issues isn’t worth it if nobody's been maintaining the system since 2008.

Answered By TechWizard99 On

Yeah, that should work! Just set up the 2012 eval, patch it up, join and promote it, transfer the FSMO roles, and then demote the 2008. After that, you can bring in 2025, promote it, transfer the roles from 2012, and then demote 2012. Just make sure to check your functional levels and replication after everything is done!

ServerGuru42 -

This dude knows his stuff!

NerdWithStyle -

This is the way.

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