In-Place Upgrade of Domain Controller Running Server 2008 R2 SP1 to Newer Versions

[medusanyc]

I have a couple of clients running Windows Server 2008 R2 SP1 and both are running Active Directory on these servers and they are the Domain Controller in a single server environment.  I think both would prefer to not purchase new servers as they replaced all the hard drives in those systems a couple of years ago and they might not be a position to purchase all new servers right now.

Is it possible to perform in-place upgrade these domain controllers from Windows Server 2008 R2 SP1 to Windows Server 2012 R2 Standard?  I read this post https://bit.ly/2NpbzBi and it seems the only upgrade path is to Windows Server 2012 Standard (that post doesn't mention anything about the domain controller role and upgrading).  Is that even available for purchase?  All listing I found for Server 2012 seem to be R2 version.  

I know the recommended path is a new server running the latest OS but is it possible to perform a successful inplace upgrade to later versions.  I've read that evaluation copies of server 2012 can not work when machines are running as a domain controller.  

I have done a little research but really can't find 100% confirmation of what my options are based on the roles these servers play as domain controllers.

Any clarification and list of options would be appreciated.  

Thank you

Andy Bernstein

[#2 · Accepted solution]

Yes, an in-place upgrade is possible 2008 R2 --> 2012 R2 but not recommended. 

https://docs.microsoft.com/en-us/windows-server/get-started/installation-and-upgrade

The fact that it is a domain controller does not change anything, it just makes it a riskier move. If you must then I'd check that domain health (dcdiag / repadmin tools) and operating system health (checksur tool) are 100% before beginning, and that it's patched to latest cummulative updates. (please don't post logs here) If help needed along those lines then start a new thread. I'd also make sure to have on hand known good bare metal backup just in case, and lastly check here and with manufacturer about operating system support for the hardware.

https://www.windowsservercatalog.com/

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[#3]

@Dave Patrick 
Thank you for the prompt reply.  Guess this chart on this page (https://bit.ly/2NpbzBi) made me think that one could not upgrade from 2008 R2 SP1 to 2012 R2.  I must have missed the Server 2012 R2 section on the upgrade and installation page.

Not sure how soon we will be doing this but just wanted to make sure as I remember reading the following in regards to evaluation version of Windows 2012 R2 server and domain controllers: 

If the server is running an evaluation version of Windows Server 2012 Standard or Windows Server 2012 Datacenter, you can convert it to a retail version as follows:

1. If the server is a domain controller, you cannot convert it to a retail version. In this case, install an additional domain controller on a server that runs a retail version and remove AD DS from the domain controller that runs on the evaluation version
   https://bit.ly/2G97sCz

That made me wonder if there were any restrictions regarding an in place upgrade of a 2008 R2 SP1 domain controller to the full retail version of Server 2012 R2.  

Can you point me in the direction of the commands to use to check the domain health.  I found the Checksur page and downloaded the proper version.  There is no problem running the Checksur tool if there are no update issues?

Will review all the information you provided before taking any action and will create an Intelligent Disaster Recovery backup in the Backup Exec software we are running or some type of image backup prior to any in place upgrade.  

thanks again

Andy Bernstein

[#4]

You can only do an in-place upgrade from a licensed windows instance using retail or volume media. You cannot use evaluation media to perform an in-place upgrade. Also it isn't supported to convert an evaluation instance to licensed for a domain controller.

[#5]

@Dave Patrick 

I have one last question, Can a new server running Windows Server 2019 be joined to an active directory domain that is currently running on the 2008 server?  Is there any special needs that have to be addressed to add the 2019 server to the existing domain...

Thank you

You have been very helpful. 

[#6]

Yes, that should not be a problem to join 2019 member server to 2008 domain.

(please don't forget to mark helpful replies)