Upgrading from Windows Server 2008R2 to ?????

So like many professionals, I am sure there are plenty of old servers inside of your environment. In my current environment, we have a really large amount of 2008R2 servers. We are also in the middle of transitioning our core infrastructure from Xen to VMware. You can check out my other blogs on that topic here.

The biggest caveat to upgrading any server is which version do you upgrade to. With 2008R2 reaching EOL at the beginning of 2020, there will likely be at least 4 versions to upgrade to by then. Currently as of this writing, there are already 3 versions (2012R2, 2016, 2019). I'm not including 2012 for obvious reasons because that would be like installing just 2008 instead of R2. So what's the easiest in my opinion? My answer: 2012R2.  I'm sure some are going to be like WHATTTTTTT?!?!?!
Don't worry, I'll explain.

So 2012 R2 will reach it's EOL in 2023 and that's almost 5 years away. Let's all be honest with ourselves, we transition servers and environments so frequently that there's a whole lot that could happen in 5 years. So that being the case, the easiest transition and supported upgrade path would be 2008R2 > 2012R2.  Using this upgrade path, allows you to keep all software in tact. You don't have to worry about reinstalling most software packages and most roles and features will also transfer. You cannot upgrade from 2008R2 > 2016 or 2019 and keep the software packages. It will give you a fresh install.

I have upgraded file servers, license servers, and print servers from 2008R2 to 2012R2 with no issues other than few minor updates that were needed. There's a bug that appears to only happen on a few servers, but if you upgrade from 2008R2 to 2012R2 then Server Manager may crash repeatedly. This is due to an issue with .NET. If you install at the writing of this blog .NET 4.7, then it will stop crashing. This particular issue has only happened on a few handful of servers so it shouldn't be expected each time.

So what about upgrading 2012R2 to 2016 after the 2008R2 upgrade? This is a totally doable upgrade path as well. In fact, I totally recommend it. 2016 EOL is 2027. So how do you know which is the best path to reach for? That's really not a simple question. You should base it on your environment and what you have installed. If it is a raw server with nothing installed except for roles and features and data, then I would totally go from 2008R2 > 2012 R2 > 2016. If we are talking about a worker server such as a Citrix VDA server, then I would totally do 2008R2 > 2012R2 > 2016.  However, I would test 2012 R2 and verify that all the software installed still works. I would then upgrade again to 2016. Reinstall any Citrix Components (PVS Target, VDA, etc) and boom now you have an upgraded 2016 environment.

If you are on a virtualized platform, then I totally suggest the BCDEdit method of upgrading a Citrix PVS Image. It is literally the easiest method since booting directly to the PVS image by using NFS or CIFS as an SR. If you want more information on the BCDEdit process, then I'll be posting one soon on the subject.

So is there an easier way even better than this? Yep. If you have a server that has nothing installed except roles and features and data is on a different drive, then I would build a 2016 server. Install the same roles and features, then move the data drive to that server. Now you are done and you didn't have to install anything on top of your existing server.  There are many different methods to this madness. You just have to find the one that works best for you. In these situations, the biggest thing to remember is TEST. Also, it is much easier to do this a virtualized environment. For those of you, that still have a lot of physical servers, you need to really jump on virtualizing your environment. You can either build out a virtualized on-prem environment or move everything to the cloud. I might write a blog about on-prem vs cloud based virtualization and how I feel about them later.  

Well that's all I have for now, until later!!!!

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