Surviving the Skype for Business to Teams Transition, for the IT Pro

Okay, so you’re an IT Pro who does Skype for Business stuff, and you’re a bit freaked out by Teams and a reduction in your demand. Worry not! First have a crack at my previous posts aimed at the organization and IT department.

In the organization post, I point out that SfB on-prem isn’t quite dead yet. In fact, it won’t be for a while. Feel free to do nothing, and you should have a number of years of success with SfB on-prem skills. However, if you do that, at some point you’ll find yourself in a career cul-de-sac.  Don’t do that! (But do read Will Rowe’s book, it’s good, and I’m not getting paid to say this). As the book title suggests, you need to evolve or your career will die.

Did you see a ton of stuff in my two previous posts that you could pick up as skills, and stay on top of your game? You should have! If you’re the gal or guy who can confidently answer questions about how Teams works, what a SfB to Teams transition might look like, and how to help navigate your organization or IT department through that, you are in a great spot!

Other than focusing on learning what I’ve already covered, here are some other suggestions for you to consider.

If you’re on on-prem IT pro, get thee to the cloud! Learn the basics of Office 365 and hybrids. You can follow the learning paths for exam 70-346 Managing Office 365 Identities and 70-347 Enabling Office 365 Services. Microsoft is all about the Cloud, and you may find you need hybrid configurations for migrations, compliance, or to appease office politics.

Do you know anything about Azure? Check out this site for a great, uh, Azure overview. You can also get a free Azure account, which gives you no excuse for not expanding your knowledge. While Azure may not be directly related to SfB and Teams, it’s full of Bots/Machine Learning/AI, IoT, and other great stuff that does, will, or could (if you make it) integrate with Teams and drive value. You knowing about this stuff makes you more valuable that someone who doesn’t have a clue how the Bot Framework and what you can do with it and Teams.

Security and compliance are also big deals. GDPR is everywhere right now, and even if you’re not in Europe it can most certainly apply to your organization. Knowing how GDPR (or any other compliance regulations) applies to Teams gives you an edge and keeps you relevant.

Microsoft is Cloud first, Mobile first, which means that anything you can learn about mobile devices and clients will help you. Go find out how MFA (MultiFactor Authentication), Conditional Access, and MDM (Mobile Device Management) and impact not only mobile phones & tablets, but also laptops and boring desktop PCs. If you’re an iPhone user, get your hands on an Android and figure out how SfB, Teams, MFA, CA, and MDM work on the “other” platform. Likewise if you’re an Android user. Only knowing about half the major mobile platforms makes you LESS that half as useful as someone who knows about both.

And lastly, much my last IT department focused post was network centric. If you don’t have your CCNA, consider working towards it. Once upon a time to get your MCSE you had to write a “Network Essentials” exam. CCNA gives you that knowledge and more. You don’t have to be a network guy working on Cisco gear to derive value from the CCNA classes or certification. CCNA is full of background knowledge, and the part that’s “specific” to Cisco gear isn’t that specific since almost everyone copies Cisco’s interface, or is “influenced by an industry standard interface” as I’ve heard one vendor explain it.

The bottom line is that IT evolves, and this is just another evolution. SfB used to be Lync, which used to be LCS, which used to be OCS… Go learn something cool!




Surviving the Skype for Business to Teams Transition, for the IT Department

In my previous post I talked about what I feel an organization should be doing during the SfB to Teams transition. In this post, I’ll cover what an IT department should be doing to support the organization.

There are several things that an IT department needs to consider when moving from Skype for Business Server to SfB Online or Teams. The biggest by far is shifting from servers – and the associated maintenance and operations – to a focus on the network. In particular, we’ve been spoiled by 1G and faster LANs with SfB on-prem. Fantastic network performance on the LAN meant we could run a bit looser, not needing to worry about bandwidth or QoS. With SfBO and Teams, that’s a different story. You should be looking at:

Internet bandwidth – is it enough? Is it symmetric, so that upstream traffic doesn’t suffer?

QoS – While it’s true that the Internet doesn’t do QoS, you can certain have your firewall prioritize traffic based on DSCP values. You should also have it classify and mark inbound traffic from the Internet, so that it’s prioritized by the rest of your network.

Subnets – Like SfB Server, SfB Online and Teams use subnets and their associated locations in a couple of spots: e911/emergency calling locations, and for Call Quality analytics and reporting. If you don’t know your exact subnets (NO SUPERNETTING!), and the areas they serve, start documenting this. If you have subnets that span locations, plan to remedy this. Spanning floors is sorta okay in a small building, but inter-building spanning is a bad thing. While e911 dynamic location isn’t turned on yet (it’s complicated, and involves life safety. And lawyers), you’ll want things ship-shape when it is.

Policies – Teams uses many other O365 services, and they include a variety of policies for things like naming, compliance, and deactivation. You need to understand what these are, and how they work, so that you can support your organization in making sound decisions. And because at the end of the day, if you don’t, you’re the ones who will have to clean up a mess of Teams with bad names and no expiration or lifecycle.

Internet Connectivity – Centralized Internet is a bad thing for Teams and SfBO. This forces traffic from branches to have to transit your WAN ($) to a central Internet breakout, then off to the Cloud. The extra distance traveled also leads to quality issues. Central Internet breakout is sorta okay in a municipal area, worse within a country, and terrible between countries. If your security department is arguing against this, you can always configure policies to allow Teams traffic locally and send Bob and Sally’s web traffic to the central breakout.

Become friends with this webpage that details the URLs and IP ranges for various O365 services.

You should fire up the bandwidth calculator often. And maybe do a Network Readiness Assessment.

How about a handy Network Assessment Tool.

And who doesn’t want Success with Teams? So get started with Skype and Teams!




Surviving the Skype for Business to Teams Transition, for the Organization

By now you’ve probably seen and heard all kinds of rumors, leaks, plans, guidance, announcements, and roadmaps for Skype for Business and Teams. Well, here’s one more! In this post, I’ll focus on what I think organizations should be doing over the next couple of years.

Yup. Years. One of the first things that you should do, is Keep Calm and Skype (for Business) On. There is no “end of life”, “sunset” or “get off or else” date for SfB.

If you visit the Microsoft product lifecycle pages, you can see that SfB Server 2015 is in mainstream support until October 2020, and extended support until October 2025. We know that Skype for Business Server 2019 is coming later this year, and that’ll take you a few more years out for mainstream and extended support. At Ignite last year, an attendee asked if SfB Server 2019 was the last planned version, and the response was that was “unlikely”.

If you’re looking at SfB Server 2019, be aware that there are a few changes. Alas, the list of changes keeps changing, so until the product is finalized there will continue to be some speculation. You can view the Ignite announcement from last year as a general guide to what to expect, though it has been announced that Standard Edition will be available for SfB Server 2019.

So what kind of things should an organization be thinking about then? Well, in case you’ve missed it, Microsoft recommends that you pilot Teams. I have to agree. I was iffy a year ago, but the product has seen massive feature updates since then, with many more to come. The collaboration experience of working within Teams is entirely different that other application and platform combinations from Microsoft and other parties. I find myself spending more time in Teams. If you’re not currently piloting teams, check out and then start your evaluation.

Teams features compliance, security, extensibility, collaboration and mobility stories that are unmatched by other platforms.

If you’re wondering when Teams will have all of the features that you current get in SfB Online, check out this page.

If you’re looking for guidance on how to pilot Teams, this is the spot along with this page.

And if user adoption is important to you (that’s a rhetorical statement! User experience, training and adoption are key!) follow Karuana Gatimu on twitter. Karuana is the Patterns, Practices & Adoption PM in Microsoft Teams, and is a wealth of knowledge.

Is this the end of Exchange UM?

In a post on the MS Exchange Team blog, the Exchange team lays out alternatives to a service that is being discontinued. The service in question is using a SBC (session border controller) to connect a 3rd Party PBX (Avaya, Cisco, Mitel, anything not SfB) to Exchange UM online. The sunset date for this service is July 2018. The alternatives listed were to move to SfB, use an API, or to use a different voicemail system.

A couple of days ago, an update was provided that indicated that the 3rd option, to use an API, was no longer recommended. After some time, the wording was changed to indicate that it was only recommended as an interim solution. A little bit later, the post vanished. Throughout, there was anger and confusion expressed online over the change in guidance, and the lack of notice provided. Some people have since reported that they’d be informed that the post was an error.

What are we to make of this? First, if the post was in error, I find it challenging to believe that the content was in error, vs the timing of the post.

I say this, because Exchange UM is going away. Let’s look at the facts:

  • SfB is the #1 voice platform that uses Exchange UM. SfB Online has its own voicemail platform now, including auto-attendant functionality.
  • I went looking to see the last time a feature was added to, or updated in, Exchange UM. I went waaaay back, far enough back that I was convinced that the Exchange team would really appreciate it if someone could take UM responsibility off their hands.
  • According to users should have an Exchange Enterprise CAL to utilize Unified Message. For organizations who only needed the license for UM, this was a tough payment to make.

The leaked/early announcement that 3rd Party PBX support via API was no longer recommended is, to me, the nail in the ExUM coffin. If the only recommended solutions from the Exchange team are “move to SfB” and “go find another voicemail platform”, then I can’t see that ExUM is sticking around.

Getting rid of Exchange UM online is a huge task. Microsoft is slowly chipping away at the number of organizations doing 3rd party integrations, to make the eventual service termination have the least impact possible. Providing this kind of guidance before service termination plans are finalized and announced is smart. It allows Microsoft to track their success in reducing the use of the services. If the use of the services is too high, they can adjust the messaging and deprecation tactics to increase the number of organizations pursuing alternatives. Dates for service termination can also be adjusted much more easily on internal roadmaps that haven’t been announced.

I expect that we’ll see more details once the specific features for SfB Server and Exchange Server 2019 are released, though online roadmaps may have a different timeline than their on-prem counterparts.

Microsoft did provide one year of notice before the planned retirement of the “SBC to Exchange UM” solution. While I expect at least a similar amount of notice before the loss of all 3rd party connectivity to Exum, I would also expect to see a block put in place on new organizations using this functionality, while those using it are encouraged to find alternate solutions.

If you are an organization with a 3rd party PBX and you are using Exchange UM online, you should be proactive and consider your possible next steps now. Don’t wait for Microsoft to re-post this announcement, you’ll only have less time to plan.

If you are an organization with a 3rd party PBX and you’re considering using Exchange UM online, you should move quickly to avoid any block that may be put into place. You must also consider this as an interim solution while you migrate to another (like SfB) lest you suffer the indignity of having to migrate off of a solution that you’ve just rolled out.

In either case, there’s no need to panic, but you do need to make sure you’ve got this on your roadmap. You can keep an eye on here for updates on this, as well as the pending 2019 release of SfB and Exchange.


TLS 1.2 and Skype for Business

By now you’re probably heard a lot of grumblings about the insecure nature of TLS 1.0 and and 1.1, and that everyone should be moving to TLS 1.2. Let’s talk about TLS 1.2, SfB, Office 365, and related things.

What’s TLS?

TLS stands for Transport Layer Security. TLS is the successor to SSL, Secure Socket Layer. You can read a nice multi-part overview of SSL/TLS here
that includes details on vulnerabilities and attacks. In a nutshell, TLS is the protocol used to encrypt your stuff.

The challenge

IT has an ongoing challenge of ensuring that related systems are at compatible levels. With TLS, the idea is to enable TLS 1.2 AND disable earlier, less secure versions. It’s plain silly to leave the less secure versions enabled, unless you’re still in transition to TLS 1.2 and need the lower levels for compatibility.

About PCI Compliance

When people say PCI, they probably really mean PCI DSS, or the Payment Card Industry Data Security Standard. These are the rules that credit card processing companies say you need to follow. They’re a good read, and probably worth following even if you don’t process payments via card. You can read more here

SfB and TLS

At present, SfB does not support TLS 1.2. Microsoft is late to this party. You can expect an up-coming update to permit SfB to run on TLS 1.2 with less secure levels disabled. A word of caution however – if you have third party software for something like a call center, user/number management, e911, or whatever, make sure that it also works in a TLS 1.2-only environment.


LPE is Lync Phone Edition, the software and hardware standard for the previous edition of phones. Common model numbers are the Polycom CX500, CX600 and CX3000. HP and Aastra also make some models. All LPE phones run the same software, based on a super old version of Windows CE. This version does NOT support TLS 1.2, so if you need to run only TLS 1.2 now, your LPE devices need to be replaced. There was rumour in the past that Microsoft was looking at updating the LPEs to be able to run TLS 1.2, however I’ve not seen any official word or any updates that they’re still looking at the issue.

PLEASE don’t be one of those organizations that buys a pile of cheap used LPEs. You’ll only regret it when you have to replace them, deploy a new phone management solution, and retrain your users.


There is a tonne of material on Office 365 TLS 1.2 here  that you should review. While this article is relatively short, it’s chock full of links to more detailed resources.

More SfB and TLS 1.2 news here when it’s available…

Office Online Server/Office Web App Server Pool Certificates

I’m working on a deployment that’s using a farm of OOS servers behind a load balancer (actually, behind a high-availability pair of load balancers!) for high-availability. If you’re just using one server, this is a great guide to what you need to implement. If you’re using a farm with 2 or more servers behind a load balancer, there are a few more considerations.

To start with, the subject name on the certificate needs to be the URL that you’re defining in the SfB topology. You might use, for example. Now the fun part – the first SAN listed on your certificate also needs to be

Everything will work at this point, but you don’t have a very good high-availability story. The load balancer will need to be configured to monitor each server in the farm to determine if the server is functional. Otherwise, a server could stop functioning and the load balancer would continue to send traffic to it – that’s no good. The load balancer will most likely monitor the servers by trying to access (and the same thing for oosnode2, etc.), and watching for a 200 OK to be returned.

Most load balancers have setup wizards that will set the monitoring up for you as part of the configuration process for OOS, SfB, Exchange, SharePoint, and more. Check the vendor’s website.

In order for the HTTPS request to to success, needs to be a SAN on the certificate. The same holds true for the other servers in the farm.

You could cheat and monitor your OOS servers by using HTTP and thus not require a certificate. This is a bad thing to do. You should be monitoring the actual URL that will be accessed on the server for a true indication of the server status.

To summarize, your OOS certificate needs to have:

Subject Name (SN) of the URL you will use in the SfB topology, such as

The first Subject Alternate Name (SAN) needs to be the same as the SN.

Then, you’ll need a SAN entry for each server in the farm, such as and



Teams And SfB, (oh my) but no Lions or Tigers

Ignite 2017 has wrapped up, and for those interested in Skype for Business and Teams, it was either exciting or frightening. Microsoft is very definitely about to unleash a bump in the net, but there’s no reason to be afraid!

Over the next couple of posts, I’ll recap what was announced in the SfB and Teams space at Ignite – and since Ignite, then I’ll cover what this means for organizations using, or thinking about using, SfB and Teams. Finally, I’ll wrap with a bit of a strategy for IT Pros who might be wondering what just hit them, and what’s next.

Teams is NOT Replacing Skype for Business. (Yet)

There was some discussion prior to Ignite, fueled by an accidentally-released banner message for some Office 365 users, that Teams was replacing Skype. For some, panic ensued. The reality is that Teams is not capable of replacing Skype for Business, and as there is no Teams server for on-premises deployments, Teams could not replace SfB on-prem.

Presentations at Ignite and in the roadmap released shortly after, made Microsoft’s intentions clear: while Teams is the future of Microsoft’s “Cloud first, Mobile First” strategy, Skype for Business is not going away.

Skype for Business Server Roadmap

The next version of on-prem SfB, Skype for Business Server 2019, was announced at Ignite. The highlights of the next version are:

  • There will only be one edition, with Standard Edition being eliminated.
  • There is no director role.
  • There is no PChat role.
  • Only Server 2016 and SQL Server 2016 will be supported.
  • No in-place upgrades.
  • Upgrades from 2013 and 2015 are supported, and as in the past, only two versions are supported in an environment.
  • The 2019 client will be C2R only, no more MSI

SfBS 2019 is based on the SfB Online code, which will allow for a significantly improved hybrid interoperability story. This is also likely behind some of the role removals outlined above.

For Teams, the roadmap announced in late October is all about driving toward feature parity with Skype for Business, including:

  • Better IM chat controls
  • Contact Groups
  • Unified Presence between SfB and Teams
  • Federated Chat
  • Tonnes of updates to the meeting experience
  • Most SfB calling features brought to Teams
  • Support for calls between Skype Consumer and Teams

You can see the full roadmap here

Up next: Guidance for organizations.