EDIT 06/30/2017 - With the recent release of CU5, and brief waiting period after its release, Skype for Business Server 2015 is now officially supported on Windows Server 2016. Check it out, and happy installing: https://support.microsoft.com/en-gb/help/4015888/how-to-install-skype-for-business-server-2015-on-windows-server-2016.
While Windows Server 2016 has not been a supported operating system for Skype for Business Server 2015, there have been no shortage of people testing out Skype for Business installs on Windows Server 2016. After all, Windows Server 2016 has been out for quite some time now, and many admins are eager to get their shiny new Skype for Business environments up on something newer than an OS with "2012" in the label. 2012 was 5 years ago, after all!
There have been some recent developments in this area, though. While the developments are promising, I still see a bit of personal confusion as to whether or not Windows Server 2016 is actually a supported OS or not. Let's start with what the promising new developments are.
Note: The below paragraph previously reported that we were on CU7, but this was miscalculated, and current CU at the time of publishing this article is actually CU4.
The February 2017 CU, which is actually CU4 if you are counting, includes a very important fix that addresses silent install failures for Skype for Business Server on Windows Server 2016. Good news, right? Here is the link to the February CU for Skype for Business Server 2015:
https://support.microsoft.com/en-us/help/3207506/february-2017-cumulative-update-6.0.9319.277-for-skype-for-business-server-2015,-front-end-server-and-edge-server
For the specific KB article (KB3209566) that addresses the above-mentioned fix, check out this link:
https://support.microsoft.com/en-us/help/3209566/skype-for-business-server-2015-installer-may-fail-silently-in-windows-server-2016
Ok, great! Time to install on Windows Server 2016, right!? Well, that depends. If you are looking for an announcement from Microsoft that the specific issue with silent install fails has been addressed, then you need to look no further than the above KB. However, if you are looking for a giant green light from Microsoft stating that Windows Server 2016 is supported, that KB article and the associated CU article stop short of saying that.
So how do we find out for sure? Well, we goo look at the TechNet page for Requirements for Skype for Business Server 2015, or course, and drill down to Software Requirements:
https://technet.microsoft.com/en-us/library/dn951388.aspx
Look at the table of supported operating systems, we see the below:
Clearly, Windows Server 2016 is not listed as a supported OS. Further, if you look closely at the text below the box, you see that we are told explicitly not to use an OS if is not listed in this box. However, in the very next box below this we see the following caveat'd Note:
This adds a bit of confusion, doesn't it? It tells us that while Windows Server 2016 is not in the list right now, Microsoft is planning to add it as a supported option with CU 5. If you recall from above, we are currently at CU4, so even though we have a fix in the latest CU for install problems on Windows Server 2016, this has not quite prompted Microsoft to update their support matrix for OS's.
Note: The above paragraph was modified to correct incorrect verbage about the current CU level of Skype for Business server.
This begs the question: Is Windows Server 2016 actually supported for Skype for Business Server 2015 installs, and this TechNet article is just a case of Microsoft documentation not being updated with the most current info, or is the fact that the box is not updated a sign that Microsoft is not ready to give a fully "Green Light" on Windows Server 2016 yet? In either case, what is clear is that if you are in the group of people that really need that explicit Green Light of supportability before moving forward, it does not appear that Microsoft has signaled it yet.
Stay tuned, and I will update this blog post as Microsoft's documentation changes to shed more light on this topic.
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