Upgrading Windows Server 2008 to 2012/2016

Phil Rine
Phil Rine used Ask the Experts™
on
I have a customer with 2 Windows stand alone Windows 2008 R2 servers.  One of them is not being used and I wanted to upgrade it to 2016 as a test to see how it goes before I do the server that is in use.  They are identical Dell servers.   I know there is no direct upgrade path to Windows server 2016 so I was going to do it in steps starting with 2012.  I downloaded the evaluation version to use before going to 2016 but when I tun it it tells me that I cannot upgrade.  Is this because it is an evaluation version?
Thanks in advance,
Phil
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DrDave242Principal Support Engineer

Commented:
Since one of the servers is not in use, do you have the option of wiping it and installing 2016 on it from scratch, then migrating everything from the in-use server to it? I'm not a fan of in-place upgrades; a clean install is always preferable.

There's something else to think about: if these servers were purchased during the days of 2008 R2, they may not be ideal for running 2016 (and Dell may not support that OS on them at all).
Phil RineOwner

Author

Commented:
Thanks DrDave.  I agree that a clean install is better however this is just a temporary measure until a new server is purchased.  That's why I was hoping this route would work.  I could even get away with running 2012 if I can upgrade to it.  Based on the service tag Dell does have frivers for 2012 and 2016 so I am assuming it should work.
DrDave242Principal Support Engineer

Commented:
What's the specific error you're getting when trying to upgrade? Can you provide a screenshot of it?
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Phil RineOwner

Author

Commented:
This is the error message I get.IMG_20191212_163809.jpg
Your hunch is correct - you can't upgrade to an evaluation version.
Phil RineOwner

Author

Commented:
Thank you very much!
Phil RineOwner

Author

Commented:
Thank you both very much for your input!
DrDave242Principal Support Engineer

Commented:
One other thing: you also can't do an in-place upgrade from an installation with a GUI (Desktop Experience) to Server Core, or vice versa...or at least, Microsoft says this is not supported.

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