Skype for Business Server 2015 Support for Windows Server 2016

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.

Persistent Chat: Challenges vs. Benefits

No, we are not discussing that office worker that tends to yack your ear off like Kelly Kapoor on The Office. That would be Incessant Chat. We are talking about Persistent Chat!

This post is a very brief one. We are simply going over some pros and cons, or rather challenges and benefits, to implementing Persistent Chat in your Lync Server 2013 or Skype for Business Server 2015 environment. For those of that need a brief jogging of the memory, Persistent Chat is what was previously known as Group Chat in Lync 2010. It enables chat "rooms" where the conversation persists independent of the participants. For instance, User A can come and go from the chat room, but the conversation will  go on without that user, and the previous conversation involving User A will remain in the room regardless of their involvement. Yes, it is very cool indeed.

Challenges

So, what are the challenges associated with implementing Persistent Chat? Well, there are some things that are simply good things to keep in mind, and others that are indeed challenges. For this sake of this list, though, I am going to list them all together into one bullet-ed list.

• In an Enterprise environment, Persistent Chat cannot be collocated on the Front End Server. This means that if you are planning for Persistent Chat, you will need to plan in additional servers. Persistent Chat (PC) also requires a backend database. This database can live on the same SQL instance as your other roles, so you don't necessarily need another server for this role, but you should make sure your SQL server has enough computing power. The only case where you can collocate the PC role with the Front End is in a single-server Standard Edition build, in which case the PC SQL backend is simply another database in the existing SQL Express instance on the Standard Edition server. Of course Microsoft recommends that such an environment only be used for Demo and POC purposes, but anyone in the industry is well aware that these environments are used in production for MANY smaller businesses. If you are one of those smaller businesses, make sure you have enough RAM and CPU power on that server!
• The ability to partake in PC as an end user depends upon group and room membership. This membership is managed on the Room  level by the Managers of the room. In order to create a room, as user has to be added to the Creators group for a "Category", which is setup in the Skype for Business Control Panel. To manage these Control Panel settings, and  to create Categories and assign Creators, a user needs to be a member of the RBAC role Persistent Chat Administrator. Once a room is created, managers must be assigned per room, and those managers can then add Members. As you can see, there is quite a hierarchy that must be accounted for when deciding how use of Persistent Chat will be managed and administered within your organization.Will your chat rooms just be "open"? Will users need to submit tickets to a central Help Desk team to gain access to any rooms? Will more granular controls be required?
• A separate web interface is required to manage individual rooms, Managers, and Members. While this interface is fairly simple and  straightforward web portal that is managed through the Skype for Business client, it is yet another interface to be aware of, and to learn. This is not overly burdensome, but may require a bit of end-user training for those who will be "Managers".

Benefits

Alright, so, the challenges weren't too bad, were they? Nah. Now for the benefits. I am sure many of you have already started compiling into your own mental list.

• Many teams may have slightly different use cases for PC, but despite these differences, most of these teams share the commonality that having a central chat room for their  team  to work out of in real-time is a key component to enhancing internal communication and increasing efficiency. Having the leadership of a time buy into the added benefit of this tool will not just deliver this enhanced productivity - it will also increase end-user adoption of the Skype for Business product as a whole.
• Many teams run a 24-7 shop, meaning they have at least 3 shifts working around the clock, and such a structure usually include some sort of shift hand-off. Imagine how seamless and more complete this hand-off would be if all teammates were using a Persistent Chat room throughout their shift, recording all the happenings (good and bad) of that particular shift. Suddenly, Johnny ThirdShift won't be caught off-gaurd when an unhappy customer calls in to get the status of a down server when Suzy SecondShift forgot to mention that at turnover time.
• Enhanced productivity means less time spent trying to track down various bits of communication. If less time is spent tracking things down, or looking for an available tech to escalate to ("Hey, anybody in this room that can help me out"), workers can be more productive. This eventually translates to cost savings, which in turn means greater revenue.
• There are also "Auditorium" rooms. These rooms have a Presenter, who can essentially broadcast messages to a room with many members. While the members are not able to participate in conversation, they can closely follow the messages broadcast by the Presenter. This is especially useful in situations where there is a major outage, and several teams are trying to coordinate and work together to track the status and keep up with the latest developments of the issue. 

As you can see, Persistent Chat is not just as simple as flipping a switch on in your Control Panel, but depending on your company's needs, it may be well worth it to invest the extra planning into making Persistent Chat a part of your company's collaboration strategy. I hope this proved helpful for those of you currently weighing this decision. For others that have implemented it, and found additional Challenges or Benefits than what I have listed above, we would love to hear about your experiences! Drop a comment below!

Stay techy, my friends!

Skype for Business Install on Windows Server 2012 R2: Don't forget KB2982006

Hello all! It's been a busy start to the week, but I wanted to take a quick moment to share a tidbit of knowledge I have run acrosse while installing Skype for Business. Here is the scenario:

• Setting up a small lab with Rackspace Public Cloud VMs.
• Deploying a Standard Edition install of Skype for Business
• Server OS is Windows Server 2012 R2
• Server has been added to AD Domain
• All Windows & Security updates have been installed
• All Prerequisite Roles & Features have been installed
• Administrative Tools were installed
• AD  was prepared by extending Schema, preparing Forest, and preparing Domain
• Prepare First Standard Edition Server step was successfully run
• On the Install or Update Skype for Business Server System step, Step 1 completed successfully

Then, the problem: Step 2 failed with the error stating that not all prerequisites had been met, and it cites the KB article 2982006. This update was not picked up my the local OS when checking for updates, apparently, but is required by Skype for Business Server for install.

Now, to obtain the update, you can start the download process by clicking on the "Hotfix  Download Available" button here: https://support.microsoft.com/en-us/kb/2982006. Once you do this, though, it is not a direct download. You are prompted to first select the proper download, which should be the x64 version of the download, and then you must enter your email address. Within a few minutes, you should receive an email from Microsoft with a link for a direct download of the hotfix. This email also includes a whole lot of warnings about backing up your environment and disclaimer-like information. In my case, this is for a basic lab, so I pretty much ignored all the fine print, and just installed the hotfix. It DID NOT require a reboot.

Once you have installed the hotfix, you should be able to re-run Step 2 successfully, and on you go to Skype for Business Server 2015 testing and fun!  For any of you getting briefly stuck on this, or just planning for your environment in advance, please simply take note that KB2982006 is a prerequisite that does not get downloaded in the normal updates.

Thanks for reading!

Stay techy, my friends!