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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.<br />
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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).
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Phil Rine

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Thanks DrDave. &nbsp;I agree that a clean install is better however this is just a temporary measure until a new server is purchased. &nbsp;That's why I was hoping this route would work. &nbsp;I could even get away with running 2012 if I can upgrade to it. &nbsp;Based on the service tag Dell does have frivers for 2012 and 2016 so I am assuming it should work.
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What's the specific error you're getting when trying to upgrade? Can you provide a screenshot of it?
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This is the error message I get.<a href="https://filedb.experts-exchange.com/incoming/2019/12_w50/1438902/IMG_20191212_163809.jpg" target="_blank" title="IMG_20191212_163809.jpg (3.9 MB)"><img alt="IMG_20191212_163809.jpg" class="file-block lazyload" style="max-width: 800px;" data-src="https://filedb.experts-exchange.com/incoming/2019/12_w50/800_1438902/IMG_20191212_163809.jpg" /></a>
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IMG_20191212_163809.jpg

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Thank you both very much for your input!
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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 <a href="https://docs.microsoft.com/en-us/windows-server/get-started/supported-upgrade-paths" rel="ugc">not supported</a>.
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I have a customer with 2 Windows stand alone Windows 2008 R2 servers. &nbsp;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. &nbsp;They are identical Dell servers. &nbsp; I know there is no direct upgrade path to Windows server 2016 so I was going to do it in steps starting with 2012. &nbsp;I downloaded the evaluation version to use before going to 2016 but when I tun it it tells me that I cannot upgrade. &nbsp;Is this because it is an evaluation version?<br />
Thanks in advance,<br />
Phil
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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

Upgrading Windows Server 2008 to 2012/2016

This topic area includes legacy versions of Windows prior to Windows 2000: Windows 3/3.1, Windows 95 and Windows 98, plus any other Windows-related versions including Windows Mobile.

Windows OS

Windows Server 2008 and Windows Server 2008 R2, based on the Microsoft Vista codebase, is the last 32-bit server operating system released by Microsoft. It has a number of versions, including including Foundation, Standard, Enterprise, Datacenter, Web, HPC Server, Itanium and Storage; new features included server core installation and Hyper-V.