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Our organization (high school) is looking to upgrade our Windows Server 2008 R2 Enterprise server virtual host, hosting a 2008 R2 domain controller VM, and a 2008 R2 print server VM, to Server 2016 Enterprise.

We are looking to do an in-place upgrade to Server 2016 Enterprise by spinning up the VM on a separate virtual host and upgrading. Microsoft's documentation isn't too clear about the pathway from 2008 R2 to 2016, so is there an established in-place upgrade pathway directly from Server 2008 R2 to Server 2016? Or are we required to first upgrade to Server 2012?

Microsoft's support documentation only details upgrading from Server 2003 to Server 2008 R2, Server 2008 R2 to Server 2012, and Server 2012 to Server 2016.

  • We are looking to do an in-place upgrade to Server 2016 Enterprise by spinning up the VM on a separate virtual host and upgrading - That makes no sense. Why would you spin up a VM? If you're loooking to do in in-place upgrade why would you need a new VM? Microsoft's documentation isn't too clear about the pathway from 2008 to 2016 - That's not true, they are very clear on the supported upgrades. Additionally, your title, tags and question states Windows Server 2008 R2 but you also mention Windows Server 2008. They are not the same thing. – joeqwerty Jun 12 '17 at 19:17
  • Sorry if I wasn't clear enough. As a backup, we will be performing the upgrade on a copy of the VM so we can just wipe it and try again. I edited my question to clarify "R2". – aidanb.01 Jun 12 '17 at 21:07
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I work in a school in the UK and we are doing most of our upgrades to our servers this summer to 2016. Generally speaking, when your using enterprise editions, upgrading can be done but we usually build a new machine and transfer the roles. We run 5 Hyper V physical machines which are all 2012 at the moment and that's gonna be fun to upgrade, but as for the other machines, ours are already at 2012 (except 2 I think). We will just build new machines and transfer the roles if possible. It's always nicer to have a clean build without any remnants causing bugs and issues.

As per joeqwerty's comment, its an in place upgrade if its live. I am guessing you mean you will duplicate the machine, update it and then replace the original. As far as I remember, there is no direct route to 2016 from 2008 so would be better off just building new if possible. If you have the time and the patience to do the double 08 - 12 then 12 - 16 don't be surprised if things break! There is plenty of documentation available for all the new and changed features when you get there.

So summarising:

  • This technet post suggests that you probably cant do a direct upgrade
  • Build new machines if you can and transfer services
  • Test Test Test

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