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Ready to upgrade to Windows Server 2016?

Now that Microsoft Windows server 2016 is generally available as of October 12, 2016, everyone is ready to upgrade their servers right? With every new Operating system release there is obviously going to be a list of new features and improvements. However, are these worth it to be bleeding edge and upgrade before the next service pack? Let’s take a quick look.

New and Improved

What’s new and probably a hot item is the support of containers. No, not your mom’s Tupperware but containers like Docker. With support for Docker Microsoft is playing nice with Open source which it would normally considers its competitor. This will help the big giant if they want to be a key player in the public cloud space and compete with the Amazon and Google. If you want to know how to get started with Docker on Windows Server 2016 check out Melissa Palmer’s post .

Nano Sever is another hot item. It’s the headless server that is slimmer, faster and better than the tradition windows server. Think of it like server core mode but a lot better. You can install Nano from the Datacenter or Standard edition of windows 2016. It’s ideal for running as a compute host Hyper-V virtual machines.

Windows Server 2016 also introduces Host Guardian and shield vms. This “shields’ virtual machines and protects the data on them from unauthorized access. You can even lock out your Hyper-V admin. There are also improvements for Active directory certificate services, Active directory domain services, Active directory federation services, and Web application proxy to name a few. 

Are you Bleeding edge?

The new features sound great don’t they? But are you really going to jump on it right away? One could say I’m not using Windows server for containers or a Hyper-V host so I should be ok. However, if you're on the bleeding edge and want to start updating your servers you should know that they are a few things that have removed from server 2016.

The share and storage management not been in the MMC is no longer available in Windows Server 2016. So if you're thinking about managing servers with an older OS through Windows Server 2016 you won't be able too. You will need to logon locally to that older server use the snap in locally from that server.

Another change is the security configuration wizard has also been removed. This has been replaced by turning on all features by default. If you to manage those features, you can only do it through policy or the Microsoft security compliance manager tool.

Since this has only been generally available for about a month all the bugs and gotchas are starting to come out. Last week it was announced that there issues with running Exchange 2016 Cu3 on Windows Server 2016. If you're thinking about running Exchange 2016 on the latest version well you shouldn’t. There are known issues with the IIS host process and Microsoft says there's no workaround at this time so save yourself a headache and stick with windows server 2012.

So my advice is test, test, test and test before you go into production if you are going to upgrade to Windows Server 2016. It’s still very new out and over the new few weeks I am sure we will hear more rumblings of gotchas. 


I try and avoid the bleeding edge...give it a chance to have the first fixpack or 2 out before I adopt.

Level 9

We are just now looking at 2012. 

Level 14

Same here. 

Level 8

We're in a place where our 2012 R2 Datacenter machines running most of our virtual machines can probably be swapped out for Hyper-V Core licenses, freeing up a ton of 'old' Datacenter licenses in the process. We're just behind the 3 year refresh schedule that MS EA's try to keep us on, oh well, our business runs regardless of bleeding edge software.

Level 10

We just deployed our first Server 2016 because of the new IIS supporting services. We prefer to wait until R2 is available, and the requester fully understands why.

Level 13

yeah, I agree. We always wait until the first or second full service pack before even testing...

Level 13

I'll wait till the first major fix.  R2 and beyond.  Staying on 2012 R2 for now.

Oh, come on--Microsoft released it to the public.  It MUST be good, and safe, and without bugs.  Right?


Nope no bugs....dress that bug up and call it a feature !!

Level 20

We're only now moving to 2012R2 and getting STIGs for it and approved by DSS for many other information systems o.O!

The testing began right away, I expect that if something needs 2016 we will be ready for it shortly, but otherwise it won't be the default OS for another year or two.

Level 20

I suppose we are using 2016 for some things in the enterprise but most of the things I work on it's not ready for prime time yet...

Level 15

Downloaded and beginning to put up a test machine or two.  But agree, will wait until the first fixpack before rolling one into production.


Yea, I usually like to wait until most people have stopped complaining about it first!!  Might like to play on the bleeding edge, but not operate on it.

Level 21

We will bring it into our lab and start working with it to get a better understanding of it and how to manage it; however, we won't roll it out to production until we feel it's ready.  All of our management applications such as Patching, Anti-Virus, Monitoring, etc. all need to support the OS before we can roll it into production and support it for our clients.

Level 13

I'm not even ready to do that yet, byrona​...

Level 13

Any viable feedback on Windows 2016 polling engines? Anyone migrate from 2012 R2 successfully? Any caveats?