How Do Skype for Business, Teams, and Slack Meet Compliance Regulations?

We recently talked about SOX compliance in our regular newsletter, “WOOF!” The full article is here: 5 Big Benefits Your Company Gains from SOX – WOOF! March 2017

(Yes, there are actually benefits to SOX compliance. Weird, huh?)

It made me think of how I (very briefly) mentioned compliance in The Security Behind 6 Business Chat Apps (Including Skype for Business). Have I ever examined Skype for Business on its compliance? Not in detail, I hadn’t.

Well, since I’m thinking about it, why not? Let’s see what I can find on compliance!

What Do I Mean by Compliance?

Compliance is a term for your business meeting certain legal requirements. When it comes to communications, compliance means maintaining records of conversations, in case legal entities (e.g. government) need to review those records in an audit or lawsuit.

That means the records must include chat logs, voicemail, voicemail transcripts, and emails. Anything your employees used to communicate and direct business activity.

Library of Compliance Regulations
“Compliance requirements are clearly stated in Volume XIX Section 14, Paragraphs A-F.”
“Wait, where?!”

Several compliance standards exist: SOX (Sarbanes-Oxley), HIPAA, EUMC (EU Model Classes), ISO 27001, etc. If you have to meet one, keeping those records is now a legal requirement. Only option you have is, which solution do you go with?

There are far more potential solutions out there than I could cover in one blog post. For today, I’m covering four communications tools: Skype for Business (Server and Online), Slack, and Microsoft Teams. Let’s see how they stack up.

How Slack Meets Compliance Regulations: Compliance Reports

Good news, Slack users. Your choice of chat app has built-in compliance…and it has since 2014.

Slack has a Compliance Reports feature, which allows you to export all team communications, thereby satisfying compliance requirements.
Slack announced Compliance Reports in a 2014 blog post: Slack’s policy update: What it means for you (November 2014)

Compliance Reports is part of the Slack Plus plan. It’s available to Team Owners. The catch is, it’s NOT enabled by default. You have to request Slack enable it. (The procedure to do so is in the blog post.)

Also, Compliance Reports is NOT retroactive. Once it’s active, it begins archiving channels, private messages, edit history…from that point forward. So if you’re already using Slack, and want to add in Compliance Reports? Better copy out all the old conversations, just in case.

How Skype for Business (Server) Meets Compliance Regulations: Archiving Menagerie

Ah, my old friend. How’s your compliance?
Very good, thank you. Just needs some setup.

First, the Exchange Server. Exchange has well-developed compliance features. So much so that Exchange 2016 will archive some Skype for Business content within its own In-Place Archiving feature:

“You can archive instant messaging conversations and shared online meeting documents in the user’s primary mailbox. The mailbox must reside on an Exchange 2016 Mailbox server and you must have Skype for Business Server 2015 deployed in your organization.”

In-Place Archiving in Exchange 2016 – TechNet

Next, Persistent Chat’s Compliance service. Once activated, this service maintains an archive of Persistent Chat messages, as well as activities. When people join/leave chat rooms, upload/download files, etc.

Setup is relatively simple. You only need to use one cmdlet, configured by identity or instance.

Set-CsPersistentChatComplianceConfiguration [-Identity ] ((COMMON PARAMETERS))


Set-CsPersistentChatComplianceConfiguration [-Instance ] ((COMMON PARAMETERS))

Parameters available are as follows:

  • AdapterType – Lets you specify the adapter type (XML default).
  • OneChatRoomPerOutputFile – Lets you specify that separate reports to be created for each chat room.
  • AddChatRoomDetails – Records details about each chat room in the database. Disabled by default, since it can inflate the database with lots of activity.
  • AddUserDetails – Records details about each chat room user in the database. Also disabled by default, for the same reason.
  • Identity – Lets you scope compliance settings for a particular collection (Global, Site, Service levels). Global is the default.
  • RunInterval – Dictates the amount of time before the server creates the next compliance output file (default: 15 minutes).

Thirdly, Archiving Server.
Does your Skype for Business deployment include an Archiving Server? If not, and you have compliance requirements, you should do so right away. (Here’s how to deploy an Archiving Server if you don’t have one yet.)

Archiving Server maintains an archive containing:

  • Peer-to-peer instant messages
  • Conferences (meetings), which are multiparty instant messages
  • Conference content, including uploaded content (for example, handouts) and event-related content (for example, joining, leaving, uploading sharing, and changes in visibility)
  • Whiteboards and polls shared during a conference

My old post on what Archiving Server archives. (Hmmm, I should update that one…)

Once this three-part setup is complete, your Skype for Business Server is keeping track of its conversations. Add a good backup system, and you should be fully compliant in case of audit (or litigation).

How Skype for Business (Online) Meets Compliance Regulations: Trust and eDiscover in the Cloud

As Microsoft says in the Office 365 Admin’s Security & Compliance menu:

“It’s your data. You own it. So we’ve developed features that let you take charge of how and when it is stored, used, and retained or removed.”

Office 365 Trust Center, Compliance

I view Skype for Business Online the same way I do Slack. The records themselves are archived and available. However, since Office 365 products are cloud-based, eDiscovery becomes much more important. You’ll need to locate & extract content as-needed in the event of an audit.

Fortunately, Microsoft put up a slew of information about O365’s eDiscovery capabilities: eDiscovery in Office 365.

For instance, the Content Search tool will search mailboxes, public folders, Skype for Business conversations, and more. Then you export the results (in different formats, like a PST for each mailbox or individual messages) and incorporate the files into your audit process.

How Microsoft Teams Meets Compliance Regulations: Information Protection…But is it Complete?

The Teams FAQ reports that Teams does retain all messages. We also have this:

What forms of information protection does Microsoft Teams support?
Archiving, Content Search, eDiscovery, legal hold, and audit logs are available via the Office 365 Security & Compliance Center for chats and channel messages, OneNote content, OneDrive for Business files, and SharePoint content.

At the same time, compliance tools are listed as “Working on It” here:
Commenters spoke urgently of the need to confirm Teams’ compliance policies.

Now, that could just be out of date. The FAQs are maintained, so they’re likely the latest-and-greatest information. Especially since Teams is an Office 365 product, which is compliant with several industry certifications anyway. The same eDiscovery tools available to Skype for Business Online, are available to Teams. At least according to Microsoft.

Compliance or Lawyer Visit
You don’t want a visit from someone wearing these. Stay compliant!

My Verdict: All Will Meet (Most) Compliance Regulations As-Is

In terms of compliance “thoroughness,” I’d rank these in the following order:

  1. Skype for Business Server. The most work to set up, but the most control over archiving.
  2. Slack/Skype for Business Online. Less work involved, since most of the archiving is done for you, and retrieval features are available. That said, these do use cloud services, which places (most of) the data outside your network.
  3. Teams. I put this one last because it’s still so new. It does fall under Office 365’s Trust Center guidelines, and does facilitate archival. But since it’s in early adoption stages, the need to verify compliance hasn’t come up in large numbers yet. Will Teams fully satisfy legal compliance for the businesses who use it? I think it will…but we may have a few businesses hitting bumps when they begin an eDiscovery process.

How big of a factor is legal compliance in your communications choices? Please comment or email. I’m also curious to note which type of compliance hits your business the most (if you’re able & willing to share, of course).


Teams vs. Skype for Business: Which to Choose?

A tug-of-war is brewing among Microsoft users. (I wouldn’t call it a ‘war’…we’re all reasonable folks, right?)

The question is, which app do we use: Skype for Business, Teams, or both?

Different Apps for Different Communications

Looking at them in terms of approach, Teams and Skype for Business are quite different.

SKYPE FOR BUSINESS: A server-based or cloud-hosted platform meant to replace phones, give the office full Meetings capability, and connect a suite of communications tools to Office apps & email.

TEAMS: A cloud-hosted chat-based communications tool (with extras, like Online Meetings), adding onto the existing toolset. Also connects with Office apps.

Office Chat
The online equivalent of this should be just as easy to arrange. Photo by Chris Hunkeler

Ostensibly, each element in those descriptions would influence a business’ decision to adopt. You might even consider using both, given their respective strengths.

Problem is, there’s also lots of overlap. Too much to make a decision easy.

If you’re looking at Teams and currently use Skype for Business:
You might think, “We already have most of the tools. Why add more?”
Hearing from users who have both, we know that they experience 2 sets of notification alerts. They’re often confused over which tool to use for calls or meetings. They also have 2 sets of conversation history to deal with (1 stored in Outlook, the other in Teams’ channels).

If you’re looking at Teams and don’t use Skype for Business:
You may ask, “Do we want to try out this chat app instead of Slack/Hipchat/Workplace?”
Teams is good to start with, IF you already use Office 365. But even then, you’ll still need a phone for PSTN calls. You can use cellphones of course, but those offices with phones already (either PBX or VoIP) can’t power them with Teams.

This leaves users with a befuddling choice. One we’ll address later in this post. But first, let’s imagine a scenario…what if you combined the two?

Is Integration Possible? Yes…But the Form it Takes Determines Usability

Because Teams and Skype for Business overlap so much—on chat, PC calls, online meetings—the biggest difference between them is the few features the other DOESN’T have.

If you were to enhance one of them, including all of the other’s features? They would look like this.

Teams Enhanced: Calls can go anywhere (including the PSTN). Chats and Meetings with internal & external users, in the same number of steps. Presence status indicates when someone is active on their computer, not just in Teams (Displaying Status in Teams – MS Tech Community).

Skype for Business Enhanced: Persistent Chat acts more like Instant Messaging. Total control of chat within Skype for Business client. Closer/native switching between Persistent Chat & other services (e.g. conferencing).

Could the two integrate? Yes. Would that result in the ‘enhanced’ versions I mentioned? Possibly, depending on the avenue taken.

Right now, I can see two such avenues:

  1. Integrate Teams’ chat space into Skype for Business. Matt Landis has illustrated this wonderfully over at his blog: A Concept for Integrating the Skype for Business & Microsoft Teams User Experience
  2. Build the remaining Skype for Business tools into Teams. Many users are clamoring for this over in the Teams forums: How can we make Teams Better? – Complete Skype for Business Integration into Teams

Neither seems easier than the other, from a development perspective. But both are desired. Users see two types of communications platforms, each missing something the other has, and want those other features.

Teams Could Not Replace Skype for Business (but Skype for Business Could Improve by Integrating Teams)

In terms of integration/replacement between Teams & Skype for Business, I’m going to make another prediction. I predict that SOME form of integration will occur between them within 2 years. Could be as simple as linking Presence; could be as dramatic as merging the two services entirely.

I like Matt’s approach. It patches Teams into Skype4B, acting as a replacement Persistent Chat. As chat is one of my favorite features, this would give Skype for Business a big usability boost.

I looked at the Office 365 Roadmap for any indication of where Microsoft’s going with Teams. Unfortunately, I found nothing specific about Teams feature add-ins or integrations. If anyone from Microsoft wants to weigh in, I’d love to hear it!

So ends my thoughts on integration. But before I finish up, let me address the choice you’re waiting on. When you’re faced with Skype for Business vs. Teams, which is the better choice?

Which Should You Choose, Skype for Business or Teams? Here’s How to Decide

Your existing business communications will contain a number of factors. Weighing these factors will help you decide which platform to use.

These questions should identify those factors. They presume that you are not currently using either Skype for Business or Teams, but want to choose at least one.

Chat Apps

  1. Number of cellphones: What percentage of employees have cellphones now (for business use)?
  2. Are office (desk) phones already in use? Yes/No
  3. If Yes, do they use a PBX or Voice over IP?
  4. Does your business have more than one office, remote workers, or both?
  5. What is your staff’s preferred communications method (besides email)?
  6. Do you use Office 365? Yes/No/Planning To

Use Teams if you gave the following answers:

  1. Percentage is close to 100%
  2. No, or Yes if #3’s answer is Voice over IP
  3. If #2 is Yes, Voice over IP
  4. Remote workers, or both
  5. Instant Messaging, Skype (consumer), texting, or chat (and you don’t already use Slack or Workplace)
  6. Yes, or Planning To

If your answers are different, use Skype for Business. You have communications needs Teams cannot (at this time) fulfill.

Above all, Teams needs the ability to communicate with users outside your organization. Without this, it’s fundamentally hamstrung and unable to mature. It IS coming, but we’ll see how well it works when it arrives.

I hope this is helpful. But always factor in your current IT systems & network capacity when deciding!

What enhancement (if any) would you like to see in Microsoft Teams? Please comment or email your thoughts.


How to Calculate the Bandwidth You’ll Need for Skype for Business

More than once, the first call we get from a new Skype for Business customer involves bandwidth. Namely, the customer doesn’t have enough of it.

Lack of bandwidth manifests in frustrating ways with Skype for Business: video freezes, abrupt Skype Meeting departures, sudden voice garbling (I’ve heard this called “demon wailing”), and the always-irritating dropped call.

When customers call with these issues, they often think Skype for Business is broken. It’s not…it’s just bandwidth-choked. Additional configuration, or a better Internet connection, and voila! Skype is doing great!

Bandwidth allocation is critical to Skype for Business planning. You’ll need to calculate bandwidth needed for each user before deployment. (You can do it after deployment, but it’s messier. Not recommended.)

What’s the Minimum Bandwidth Needed?

According to Microsoft, the minimum bandwidth requirements for Skype for Business (Server) deployments are:

Provision the network links to support throughput of 65 kilobits per second (Kbps) per audio stream and 500 Kbps per video stream, if they are enabled, during peak usage periods. A two-way audio or video session uses two streams, so a simple audio/phone connection will require 130Kbps to cover each stream. Video will likewise use 1000 Kbps total to carry an upstream and downstream connection.

To cope with unexpected spikes in traffic and increased usage over time, Skype for Business Server media endpoints can adapt to varying network conditions and support three times the throughput for audio and video while still maintaining acceptable quality.

Plan Network Requirements for Skype for Business 2015 – TechNet

For those of us who live in the real world, those are obviously minimum numbers. Day-to-day Skype4B usage needs more available bandwidth to comfortably handle office communications.

Calculating bandwidth requirements is an early step in the Skype for Business (or Office 365) deployment process. Before you calculate though, you’ll need to map out the user requirements. Can’t determine bandwidth for all users, if you don’t know how many users you’ll have on the system!

To determine user requirements, list out all these factors:

  • Number of sites
  • Number of users
  • User types: Desktop, mobile, in-office, remote, audio-primary, video-primary, heavy chat, light chat, administrators, etc.
  • Tools used (Video, Skype Meetings, VoIP, Response Groups/Call Queues, App/Desktop Sharing)
  • Estimated traffic numbers (based on the number of simultaneous users)

Okay, now we have some idea of scope. Let’s start on bandwidth.

Choose your Bandwidth Calculator

I went scavenging for the existing bandwidth calculators. I expected to find one…but I found three! Each serves its own specific purpose, though you can use all of them together to weigh your options.

The numbers I entered are based off existing Skype for Business customers. I changed a few to avoid any risk to their security. As a result, the bandwidth requirements don’t 100% match real-world usage. Just so you’re aware.

Skype for Business Bandwidth Calculator/”The Monster”
First and foremost is the Skype for Business Bandwidth Calculator spreadsheet.
Interactive spreadsheet stepping you through the bandwidth numbers needed.

This thing is a monster. It’s the digital equivalent of an airplane’s cockpit – dozens of switches, all jumping out at you simultaneously.

Make sure you download & read through the User Guide as well. It points out several notable things:

  • Only WAN bandwidth is modeled. LAN bandwidth isn’t factored in.
  • Each Site only has one WAN link in the calculator.
  • A “central Site” is assumed to have a PSTN connection, and hosts either a Skype for Business Server Front End pool, or a Skype for Business Cloud Connector Edition.
  • The calculator doesn’t account for situations where users are using the PSTN at another location (e.g. branch site) for some or all of their calls.
    • This could come about due to a dial plan configuration, or a PSTN failure at the users’ local site. Such a situation tends to happen when a critical failure occurs; make sure you consider those when planning.

I entered 2 central sites and 1 branch site, all on-prem. A 50Mbps Internet connection for the San Francisco Site, and a 5 Mbps connection for Ventura (Oakland is associated to San Francisco). The central Sites have a total of 70 users and 3 administrators; Oakland has 15 users. WAN link speed is 50 Mbps; half of that is allocated to RTC traffic, for experimentation’s sake.

RESULTS: On the Aggregated Results tab, I see that Skype for Business only needs 703 kbps (1%) of the San Francisco WAN link, and 2580 kbps (5%) of the Internet connection. At the Ventura site, it needs 1066 kbps (4%) of the WAN, and 2528 kbps (25%) of the Internet connection.

Skype for Business Bandwidth Calculator

(In reality, it will likely need more bandwidth than that…particularly for smooth video conferencing. But I now have a hard-number baseline for my bandwidth estimates.)

Office 365 Planning Tools
Network Planning and Performance Tuning for Office 365 – Office Support
You’ll find several resources for Office 365 network planning on this page, including tools. No surprise, since O365 is cloud-based and needs plenty of bandwidth to function as fast as native apps.

Spiceworks and TechNet users recommend the Exchange Client Network Bandwidth Calculator for O365 bandwidth planning. This is also a downloadable Excel spreadsheet. It’s dated—the latest Outlook version listed is 2011 for Mac—but it’s much simpler and faster than Skype for Business’ calculator. I didn’t even need a user guide (which is good, because it doesn’t come with one!).

I entered 1 Site, Heavy use, with 5 users on Outlook 2011 for Mac, 35 users for Outlook 2010 Online, and 20 users for OWA 2010. Results?

Office 365 Bandwidth Calculator 1
Less than 1 MBits/sec needed. I think most office connections can do that.

It even gives expected peak usage times too.

Office 365 Bandwidth Calculator 2

Again, this calculator is out of date. But something’s much better than nothing, and the results from this make for an at-a-glance foundation while you’re estimating traffic.

Please consult the best practices and references also listed on the above-linked page. They recommend doing a pilot deployment as a test. We often set up 5 users in Office 365 pilots; it’s enough testing to find and fix any bandwidth issues before site-wide deployment.

Teams Bandwidth Calculator
This is for Microsoft Teams, not Skype for Business. But it’s a much simpler tool than the Skype for Business Bandwidth Calculator. Just enter in some user numbers, choose an expected traffic level for discrete services (such as Conference Video Usage), and hit Calculate. Each row represents one Site.

Teams Bandwidth Calculator 1
Teams Bandwidth Calculator 2

With Teams, my numbers indicate that I’d need 3.566 Mbps. Also quite doable.

An interesting point here: The numbers don’t quite match up, but we see that Teams wants more bandwidth than Skype for Business does. I think this occurs for two reasons:

  1. Teams contains many of Skype for Business’ highest-bandwidth tools – Video, Meetings, and Calls.
  2. Notice that the WAN impact is very small; 0.058 Mbps. Teams uses Internet bandwidth much more than WAN. I believe that’s because Teams interconnects with other Office 365 services in real-time. As such, it needs a higher bandwidth allocation to “keep talking” with Microsoft servers and other client computers.

As such, I find this Teams calculator particularly useful. It’s less specific, but it’s really fast and bone-simple to use. Good way to get the network planning ball rolling.

(Can we get something like this for Skype for Business too? It would save so much time…)

You’ll find the calculator at:

Use Bandwidth Calculators Early & Often in the Skype for Business Deployment Process

One last thing: If you’re wondering about bandwidth requirements for a conference room system? The SmartTech Knowledgebase has kindly posted a detailed answer. Their estimate reflects their own SMART Room System product, of course. But that only lends credence to their 20 Mbps bandwidth requirement. Good to know if you’re equipping a conference room with Skype for Business.

Network bandwidth requirements for SMART Room Systems with Skype for Business – SmartTech

The great thing about calculators like these? You’re not wedded to the first result. Test different numbers of users, activity requirements, etc. Running a half-dozen possibilities gives you more detailed bandwidth projections for the future.

Test several models out. It only takes you a few minutes per calculation (even with “The Monster”). Then you can continue, better-informed, with the deployment process.

How do you prefer to calculate bandwidth requirements? Please comment or email. I’d love to get some more tools for comparison testing, if they’re out there.


Skype for Business Online Now Has Auto Attendant and Call Queues

After long previews (and a few delays), Microsoft is finally adding Auto Attendant and Call Queues to Skype for Business Online.

Skype for Business drives digital transformation – Office Blogs

Microsoft adds new calling features to Skype for Business – ZDNet

Let’s do a quick rundown on the new features first. I’m glad to see Skype for Business Online users getting these…even though Skype for Business Server users have had them for a while.

What the Auto Attendant and Call Queues Do

Auto Attendant is an automated system to answer and route inbound calls using dial pad inputs and speech recognition. You’ve encountered these plenty of times, when calling ISPs, telecom providers, or enterprise companies.

“To speak with Sales, press 1. To access a dial-by-name directory, please press Pound.”

Call Queues route incoming calls to the next available live attendant in the order they are received. Same deal as Auto Attendants…in fact, I don’t recall any instance where I’ve encountered one without the other. Creating both together is standard practice for all of our Skype for Business (Server) customers.

“Yes, I know you were calling for Alice, but she’s on the other line right now. My name’s Bob, how can I help you?”

Doesn’t Skype for Business Server have these features?

The question a lot of people (including some of our readers) have asked. Yes, these calling features already exist for Skype for Business Server users.

In fact, we’ve discussed them a few times here on the blog. These are the Auto Attendant-related posts:

The Two Types of Response Group Management (and When to Use Them)
Examining Lync’s Connection Tools: OCSUMUtil
Auto Attendant Failing? Your UM Dial Plan Can’t Have Spaces in its Name
Software Review: Attendant Pro (Part 1)
Software Review: Attendant Pro (Part 2) – Quick Access Shortcuts

Noted Skype for Business expert (and longtime friend to the blog!) Jeff Schertz has an excellent post addressing Auto Attendant as well: Skype for Business and Exchange UM Integration – Jeff Schertz’s Blog

Here are the Call Queues-related posts (not as many, but it’s hard to focus on one without the other):
The Two Types of Response Group Management (and When to Use Them)
Examining Lync’s Connection Tools: OCSUMUtil (Gee, sensing a pattern here…)
Lync Updates for January 2014: Server 2013, Phone Edition and Lync for iPhone All Updated
How to Create a Response Group: 20 Tasks Every Lync Administrator Must Know

Why the Delay?

Slow Update pace...deliberately?These features integrate with Cloud PBX. Which, as you’re aware, creates a telephony system in the cloud to replace your PBX-based on-site phone system.

Adding more calling features to the existing Cloud PBX – while it’s in use, no less! – would require a good chunk of engineering. Field testing them rigorously is necessary (hence the preview). Given all that, I understand the slow development pace.

What I don’t understand is why they weren’t integrated when Cloud PBX was first deployed. The functionality did exist, as part of Skype for Business Server’s voice routing capability.

Part of the O365 Adoption Strategy?

A comment on the original Microsoft announcement said something very important:

“Great news but the features still only work with on-line users and not with hybrid voice deployments.”

Still no Auto Attendant/Call Queues for hybrid deployments. So, it’s two-thirds of a launch?

That makes me think each new feature gets staggered out intentionally. Not (totally) because of development time, but because it gives them another announcement to trumpet. Each time pushing more users away from Skype4B Server, toward Office 365. Even Hybrid users will feel the push this time…and maybe next time too.

Lest you think this is just a rant (apologies for that), let me end with more useful information.

How to Create an Auto Attendant and Call Queues in your Office 365 Admin Center

As of this writing, you will need an E3 (plus Cloud PBX) or an E5 Office 365 account, to enable Auto Attendant and Call Queues.

Before setting up either feature, you’ll have to get a new number, or transfer your existing service numbers, into Skype for Business. They have to show up under “Voice > Phone numbers” with the Number Type as “Service—Toll-Free.” See Getting Skype for Business Service Phone Numbers – Office Support.

CREATING AUTO ATTENDANTS:Auto Attendant Call Handling

  1. In the Skype for Business Admin Center, click Call routing > Auto attendants.
  2. Click Add new.
  3. You’ll have four pages of options:
    • Edit General Info – Setting the attendant’s name, phone number, language & operator.
    • Select Hours of Operation – Will this attendant run 8-5, 24/7, or somewhere in between?
    • Business Hours Call Handling – Which greeting to use, what to do with calls, and which options callers must choose.
    • Select Dial Scope – Which users are included in the attendant.
  4. Enter the appropriate information for each page. You may need to create a phone number & a greeting prior to setting the attendant up.
  5. Once the new Auto Attendant is ready, click Save.
  6. Navigate to the Auto Attendants page (if you’re not already there). Select the new attendant.
  7. Click the Test button to test the new attendant.

Full documentation: Set up a Cloud PBX Auto Attendant – Office Support


  1. In the Skype for Business Admin Center, click Call routing > Call queues.
  2. Click Add new.
  3. Like before, you’ll have several options to set.
    • Call Queue Name, Phone Number, and Domain
    • The Greeting and Music to play while callers are on hold (for all our sake, pick some fun music!)
    • Which users should serve as call agents for this queue
    • The maximum queue size (default is 50, but it can go from 0 to 200) and wait time, as well as what happens when the queue is full & wait time is reached
    • Which Auto Attendant you’ll assign this queue to – You must configure the Auto Attendant before the Call Queue.

Full documentation: Create a Cloud PBX Call Queue – Office Support

Skype for Business Online/Server Feature Parity: Getting Closer!

As with all new features, many thanks are owed to the Skype for Business dev team. Now Office 365 users have the ability to route calls around the office, saving employees’ time. Like Server users.

What’s your stance on Skype for Business Online, now that Auto Attendant and Call Queues are available? Please comment or email.


The Importance of a Backup Communications Method

We back up our files, our servers, and our phones’ data. But do you have a backup for your communications tools?

The idea came up yesterday while checking tech news. Microsoft cloud services had an outage on the 21st. An authentication issue stopped users from logging into OneDrive,, Skype, etc.

It’s the second such outage in two weeks; we had a similar one on March 7.

Any outage is frustrating, whether it’s for 5 minutes or 5 days. If the outage lasts long enough, you’re faced with a decision: wait it out, or switch to a backup?

Wait, I thought. We have backups in place for data and servers. But if Skype for Business went down, we’d lose half our communications ability. Email may not even work. A backup communications method, waiting in the wings, would be a pretty prudent safeguard!

The Risk Factor in All Cloud Services: Outages Crash Productivity

These latest O365 outages remind us all of one thing: The Cloud can go down too. Slack had an outage on March 7 too, the same time as the earlier O365 outage.Broken Communications Tools

Now, while some Twitter users joked about such outages actually HELPING productivity, the fact is that when you lose a tool you use for work, your real-time productivity is disrupted. You have to stop what you’re doing, coordinate with colleagues in some other method, send emails, make phone calls…

All of which is not the work you were doing.

Now, cloud service outages are not common. Many, Microsoft included, do have redundancies to minimize your loss of service. But even with 99.9999% uptime promised, the fact remains…the cloud is just a cluster of servers. It can crash. And take your productivity with it.

It’s a reality…which means we, as good IT pros, can plan for it!

How many of us have a spare server sitting in the datacenter, a row of darkness between all those blinking lights, ready to go if there’s a crash? Most of us, I’d bet.

How then do we “have a spare ready” for communications tools, like Skype for Business?

I’m not talking about phones though. If email goes down, it’s tempting to just grab your phone and start texting co-workers. But, hold on. There’s a major reason why your phone isn’t a good choice for communications backup.

A Backup Communications Method Should Be Equally As, or More Secure Than Your Standard Tools

Why isn’t a phone a good backup communications tool? Because you may inadvertently leak corporate intellectual property, or other sensitive data, when using it.

Remember mobile security. Platforms like Skype for Business contain their conversations within a bubble of encryption and authentication. Does your phone give you that? What about hackers & malware?

Instead, consider a backup communications method that operates securely at the outset. A protected space where you can have conversations, share files…accomplish the same things you do with your day-to-day communications tools.

For example, if you use Skype for Business Server, you could provision some Office 365 accounts to use Skype for Business Online or Teams. Same kind of environment, and you can flip over fairly fast. Outages aside, this is probably the first recommendation I’d make for businesses currently using Skype for Business Server.

But what if you use Office 365, and it goes down? Keeping a Skype for Business Server configured, but inactive in your datacenter, is too costly for a backup.

The most obvious solution is one of the other chat apps.

Which one? That depends on your current environment. To make the determination, ask yourself these questions:

  • Which of the available communications platforms will let us use our favorite communication tool, the fastest? (If group chat is popular, look to Teams or Slack.)
  • Is this secure enough for what we typically share? (Consult my post on chat app security for help there.)
  • Are my users more comfortable with desktop apps, or a web-based system? (Slack has a desktop & mobile apps. Workplace only has mobile apps.)
Broken Communications
Is Office 365 down AGAIN?!

One more factor: Consider where the chat app is hosted.

“Well, it’s in the cloud, isn’t it?” Yes, but does the maker host the services themselves, or employ other cloud servers? Workplace, for instance, is hosted on the same servers as Facebook. So if Facebook goes down, there’s a good chance Workplace does too. (Oh, the outcry that would happen…)

However, HipChat is hosted on Amazon Web Services. If Amazon has an outage, then HipChat may have one too. That second-level vulnerability should factor into your decision.

Do You Have a Backup Communications Method? You’ll Want One When You Need It!

This is very much an “Emergency Planning” type of activity. Cloud outages are, like I said, uncommon. Office 365’s only had 10 outages in the past 3 years, most for less than 1 day. For millions of daily users? That’s not too bad.

We’re IT pros though. We plan for the worst, and remain pleasantly surprised when things go well. Even (especially?) when it comes to communications.

If you use Microsoft cloud services, bookmark these three links:

They’ll tell you if a service like Office 365 is down.

If you had an outage, what backup communication method would you use? Please comment or email. And don’t forget to join the mailing list!


Q&A on Microsoft Teams

Microsoft Teams is here! It was released to General Availability (for Office 365 customers) on Tuesday. I’ve already seen several reviews of the chat platform. Links to some reviews are below.

Of course we have to weigh in; what kind of Skype for Business blog would I be if I didn’t? However, this is not just another review. I was able to trial Teams internally after the release, and thought I’d do something different.

By going through the information I’ve scoured from the Web, Twitter conversations, and my internal Teams trial, I have come up with several Teams-related questions. Questions which I shall answer!

Here are the questions. You can jump to any answer just by clicking the one you want. Let’s go!

Questions about the New Microsoft Teams

How is Teams organized?
Is there a mobile app?
What are the advantages (if any) over Slack?
Can we use Teams without an Office 365 account?
Will we get a free version of Teams? How about a consumer version?
What’s the cheapest option: Slack, HipChat, Workplace, or Teams?
How’s the bot?
What kind of integrations are available?
What’s the biggest drawback?

How is Teams organized?

Teams keeps it simple, in terms of organization. Each Team has Users invited to it. Teams may set up Channels to contain their conversations. You have the option of Public or Private Channels. Within the conversations, users can share files, video calls, a Wiki, etc.

Hierarchically, it’s like this: TEAMS > CHANNELS > USER CONVERSATIONS

There’s also an Activity Feed accessible from the left-column bar at all times. It shows your @mentions, replies, etc. Very much like Workplace’s News Feed.

Teams Activity Feed

Is there a mobile app?

Yes, but Microsoft did something a little funny with this one. The Teams app is the most advanced on Android—there you can make video and audio calls. iPhones and Windows Phones don’t have this yet. I’m sure it’s coming, but for now, Android users win out on Teams features.

What are the advantages (if any) over Slack?

I find two main differences, which you could call ‘advantages.’

One: Threaded conversations are native in Teams. (Slack did add this recently.) For those who are used to Slack’s message format, this might take a little adaptation time. But for those used to forums or sites like Reddit, threads are familiar territory.

Two: The Office 365 Integration. That eliminates extra cost, extra user accounts/licenses, and installation time. It’s one more tool in the toolbox.

Want a more direct comparison? TechWyse Blog did a great infographic comparing Teams and Slack:
Teams vs. Slack – TechWyse

Can we use Teams without an Office 365 account?

Nope. Not even to try out. I used a test user from a customer’s Office 365 account to try Teams.

This makes me sad, honestly. Teams is good enough to work as a standalone product. But I guess that’s not part of Microsoft’s strategy anymore (and we just have to live with it).

Will we get a free version of Teams? How about a consumer version?

No. No plans for this at all.

Microsoft: ‘We do not have any plans for a free or consumer offering of Teams’ – VentureBeat

That could change of course. I would like it if it changed. Slack made clever use of a free version to bring customers on, and Microsoft won’t even try a similar approach? It could even be an easy avenue into Office 365.

What’s the cheapest option: Slack, HipChat, Workplace, or Teams?

The numbers are very close here. Workplace is competing on price, but we’re talking a few dollars’ difference per user.

Here are some numbers from each service. I’m going to assume a standard account type, for 100 users.

  • Workplace: $3/month per user (for the first 1,000 users)
  • HipChat Plus: $2/month per user
  • Slack: $8/month per user
  • Microsoft Teams: Depends on Office 365 account level. Office 365 Business accounts range from $6-15/month per user. Office 365 Enterprise accounts range from $8-35/month per user.

As you can see, it’s really close. Teams could end up “costing” more than the others, but you’re also getting Office 365 bundled.

How’s the bot?

T-Bot is ready to help you on load. He’s (she’s? It’s?) really quick to respond too. I fired a few standard questions at T-Bot, and he gave exactly what I needed. Much like Slackbot, Slack’s own bot (who admittedly has a cuter avatar).

Unfortunately, T-Bot lacks a sense of humor. I tried some silly questions and a philosophy question. Poor T-Bot got confused and sent me to the FAQ.

What kind of integrations are available?

Plenty! Teams comes with 150 third-party integrations available at launch. More will come.

To integrate a service into a Channel, click the plus icon in a channel’s top nav. You’ll see a popup window with available integrations.

Integrations Available in MS Teams

I integrated Asana, our project management system. It took one login and about 20 seconds.

Integrating Asana into Teams

That’s one fewer tab I need to keep open right there.

What’s the biggest drawback?

This one deserves its own section. Because there is one big drawback to Teams…and no, it’s not the Office 365 bundling. It’s an operational flaw that many users have already come across. And it’s already hurting Teams adoption.

The Damaging Flaw: No External User Access

You cannot invite external contacts to use Teams.

Teams FAQ on Guests

I have a Skype for Business user account. But it’s Server-based, not O365-based. Thus my trial account couldn’t see it, and I could not send messages “out.”

This is the biggest issue I saw people having with Teams. It just befuddles me. Limited only to O365 users? No possibility of inviting someone into a chat, even temporarily? None.

Annoyed by this? You’re definitely not the only one:
How can we make Teams better? – External Access and Federation

Adding external users to teams – MS Tech Community

This WILL hurt Microsoft. As I said, some potential users are already swearing off Teams in favor of Slack, where they can chat with external users. Now, maybe losing market share will compel Microsoft to enable external users…but a lot of people aren’t holding their breath.

Teams is Microsoft’s Most Intriguing Productivity App Yet – Engadget
Microsoft Teams goes live with new email integration, enterprise bots – ZDNet
Teams, Microsoft’s Slack rival, opens to all Office 365 users – TechCrunch
Microsoft’s Teams is almost an excellent Slack-killer, and it’s now live for O365 – Ars Technica

Teams: Feels like an Evolved Skype for Business Persistent Chat

Teams isn’t just competing with Slack. It also competes with HipChat, Workplace, and to some degree, its own Skype for Business Server product!

Here’s why I think that. The Channels, available under Teams (which are either Public or Private, as set by administrators), are basically enhanced chat rooms. Skype4B’s Persistent Chat has a very similar structure. Private messages are essentially Instant Messages. You add voice to existing Conversations. They’re even called the same thing in both Skype for Business and Teams. “Conversations.”

The other Skype4B functions—voice, meetings, IM‐were covered in Office 365’s Skype for Business Online offering. Teams adds the Persistent Chat function.

Now, that’s not a bad thing in itself. As I’ve said many times, I love using chat. But I can’t help thinking Microsoft has miscalculated here. They’re trying to replace one product with another, but hobbled it by not allowing external user access. The MS Walled Garden rears its ugly head.

We’ll see how many people decide to climb over it or not.

Do you have a Teams question nobody’s answered yet? Send it in! Add a comment or email it over. I’ll happily update this post with it. Or create a new one, if the question merits.

And please share your Teams experiences too! I’m certain we’ll come back to Teams, soon enough.


3 Ways to Start Conversations With Skype for Business Auto-Contact Links

A reader comment drew my attention to this post from way back in 2011: 3 Ways to Start Conversations With Lync Auto-Contact URLs

They asked a simple question: “Could you do this (set auto-contact URLs) with a Skype for Business ID?”

Yes, you can! What’s more, you have more parameters to work with in Skype for Business. I found several sources to help us out here, with lots of good detail. Links at the end of the post.

I’ll follow the same format as my original post. If you’re curious about adding Skype for Business links in places like emails, on a webpage, etc., this is how you do it.

#1 – Call a Skype for Business Number From Your Browser or Email

In the previous post, I mentioned the “TEL:+12223334444” link format. You use “TEL:” plus the country code (1 for the U.S.), plus the area code, plus the number. No spaces and no quote marks. The HTML structure look like this:
<a href=”tel:+12223334444″>Call 222-333-4444</a>

This format still works! In fact it’s near-universal; almost every app that can facilitate VoIP calls will recognize it, including Outlook. The TEL: link works on mobile as well.

(You might see a popup window asking you which app you want to open the TEL: link.)

Open Link in Skype for Business from Auto-Contact Link

Though we do have a caveat here. The sheer number of VoIP-enabled apps – Skype for Business, Skype (Consumer), WhatsApp, Viber, Google Hangouts, Facebook – means your computer may not associate TEL: links with Skype for Business by default. If not, and you want it to, you may need to reset the association. Here’s how to do that.

On Windows 10, this is done in Settings, under System. Click “Default Apps”, scroll down, and click “Choose Default Apps By Protocol.” Scroll until you see the “TEL” protocol. If Skype for Business isn’t the default already, click the app that is and choose it in the popup menu.

On Windows 7/8, go to the Control Panel. Choose Default Programs, and then Set Default Programs. Locate Skype for Business in the list (it may be under “Lync (desktop)”). Click the “Choose Defaults for This Program” and check TEL:.
Reference: Changing the default app used to open tel: links on Windows –

#2 – Auto-Contact Link to a Skype for Business Account Name

Now we come to the reader’s original question…initiating a call using a Skype for Business ID instead of a phone number.

Can you do this with a Skype for Business user account name? Yep! But not with the TEL: link format. And the IM: format doesn’t work too well anymore (I think it’s deprecated).

Instead, we’ll use “SIP:”.

You’d code the link like a regular email link. SIP: goes in place of the MAILTO:. Other than that, it’s exactly the same.

<a href=”″>Call Mike with Skype4B</a>

NOTE: Skype for Business’ default response to SIP: links is NOT to start a call. It’s to initiate a new Conversation. Starting a call only takes one click from there, of course. But I don’t want to mislead anyone.

This is the best way to use Skype for Business account names on websites or in emails. From the Conversation window you can start voice, video, sharing, etc.

But when it comes to meetings, there’s an even simpler way.

#3 – Auto-Contact Link for Conversations or Meetings

Links using SIP: work to start a Skype for Business Conversation. If you want to post/share a link to a Skype Meeting though, you don’t even need a special link format. You just need the meeting’s URL. To get that…

  1. In Outlook, click New Items > Skype Meeting.
  2. The New Skype Meeting window opens. Enter whatever details & attendees you want. Before clicking Send, copy the “Join Skype Meeting” link from the meeting invite.
  3. Paste the link into any email, chat, or webpage you want. Meeting links normally look like this:
    (I inserted random numbers at the end; they’re normally an auto-generated meeting ID number.)

When clicked, the computer will either open a Skype Meeting window, or take you to this message:

Open Skype Meeting Page from Auto-Contact Link

One click to the Skype for Business Web App. Either way, you’re able to access the Skype Meeting.

Auto-Contact Links Help You Get More Use out of Skype for Business

As promised, here are the sources for this post.

Depending on your computer and Skype for Business configuration, your TEL: and SIP: links may respond slightly differently. You should still get the same result; Skype for Business spawning calls and Conversation windows. I’m giving you a just-in-case warning.

This one capability illustrates a lot of how much the communications world has changed since I wrote that 2011 post. In less than 6 years, the pace of Technology exploded Voice over IP across millions of devices. Almost every computing platform out there can click one of these links and make a call.

With links in TEL: and SIP: format, you’re extending Skype for Business out even further. Customers can click a link on your website and talk to a support rep or VP in seconds. Pretty handy for a link, isn’t it?

Do you use TEL: and SIP: links with Skype for Business? In what capacity? Please comment, email, or tweet us at @PlanetMagpieIT.


Do You Really Need PSTN Conferencing?

“I have a question. Do we really need to add PSTN Conferencing on?”

This question came from a prospective customer, during our planning stage for a Skype for Business/Office 365 rollout.

I was not present at the meeting; my co-worker told me about it later. When I heard the question, it made me think a moment. DID you really need PSTN Conferencing?

Let’s explore the idea, shall we? Who knows, it might figure into your own Skype for Business planning!

What PSTN Conferencing Does

First, a little about the PSTN Conferencing feature.

The Skype Meeting tool allows people to join a meeting space using their computers, or an app on their phones. Then they can share voice, video, a desktop, a whiteboard, etc.

But what if you don’t have an app or computer available? Or you’re on the road with no Wi-Fi? How do you join the meeting?

PSTN Conferencing lets you dial into the meeting with your phone. Just call a specific number and you’re in the meeting. The PSTN Conferencing feature enables you to create the dial-in number (or numbers) within Skype for Business.

How PSTN Conferencing Works in Skype for Business Online

In Office 365’s Skype for Business Online, PSTN Conferencing is an add-on. You have to buy it from within Office 365 Admin on a per-user licensing basis.

Set up dial-in or PSTN conferencing for Skype for Business – Office Support

The add-on costs $4/month per user (unless you’re on Office 365 E5). That’s $48/year per user. If you have 100 users who need PSTN Conferencing, you’re looking at almost $5,000 per year, every year.

Now, not every user needs a PSTN Conferencing license. Only those who plan to schedule Skype Meetings or lead them will need one. Regular attendees don’t.

How PSTN Conferencing Works in Skype for Business Server

In Skype for Business Server, the feature is actually called “Dial-In Conferencing.” You need two things to make it work: a Mediation Server and a PSTN Gateway.

Enterprise Voice Calls
Hello? Is the dial plan on?

The Mediation Server is required for Enterprise Voice, and a PSTN Gateway translates signals between Enterprise Voice and a PSTN or PBX. If you want to call out, you’d need both of these anyway!

You also need to configure a dial plan, access number, and conferencing region. Once Skype for Business is deployed, that’s relatively simple to add in. The full requirements are listed in TechNet: Plan for dial-in conferencing in Skype for Business Server 2015 – TechNet.

(You can also use a third-party solution for PSTN Conferencing, if your Skype4B Server deployment isn’t set up like this. Communiqué makes one, for instance.)

We’ve had Dial-In Conferencing installed on our internal Skype for Business Server (and Lync Server before that) since deployment. I’d never thought about it as anything other than “just a part of the system.”

But as I think about it, I realize I’ve never actually used the dial-in number. Even on my phone, I’d use the app. Does anyone else?

I asked around the office. Only one person had ever used the dial-in number, twice while driving/stuck in traffic. Aside from that, we didn’t actually need Dial-In Conferencing!

How Many People Use PSTN Conferencing to Dial In?

As mentioned above, PSTN Conferencing’s core functionality is to provide a number for calling into conferences/Skype Meetings.

Here’s the question: Who will you have calling into your conferences?

Think about the purposes behind your conferences.

  1. Team status updates?
  2. Project discussions?
  3. Sales/New customer meetings?
  4. Management roundtables?

I could go on, but one thing’s clear – many purposes exist for having a conference. But do all of them require external dial-in access? No.

In fact, only #3 above would benefit from dial-in access. And that’s only if…

  1. You’re meeting with a non-local customer who doesn’t have Internet access.
  2. A regular phone call won’t suffice, and again, no Internet access available.
  3. Nobody has Skype for Business, or Skype, installed on their computers/phones.
  4. The Skype for Business Web App isn’t working.

PSTN Conferencing May Age Out of Use, in Time

Of course you’ll want to have phone numbers where customers can reach you. That’s what Enterprise Voice (and Cloud PBX) are for.

But a conferencing dial-in number suddenly seems like less of a priority. Besides, if an external user or customer did need to join your meeting, you still have the Skype for Business Web App.

I guess it comes down to Phone vs. App. What do you prefer – calling phone numbers, or using an app? It’s only my observation, but more and more people are leaning toward App.

Which makes things like PSTN Conferencing an add-on of the past.

When deploying Skype for Business, examine your user base. Consider what kinds of Skype Meetings you’ll hold, and who will attend. It may be that you can rely on apps—and not need the time/cost of installing PSTN Conferencing.

Do you still use PSTN Conferencing? What are your thoughts? Please comment or email.


Skype for Business vs. Workplace by Facebook

Time to continue our “VS.” series! This time, let’s do a comparison of Workplace by Facebook to Skype for Business.

(Previous post: Skype for Business vs. Google Hangouts)

I was introduced to Workplace during research for The Security Behind 6 Business Chat Apps (Including Skype for Business). Here’s an excerpt from that post, talking about Workplace:

The Workplace app does almost exactly the same things as Microsoft Teams and Slack: chat rooms, groups, external users, video, etc. It’s just made by the Facebook team. Pricing is cheaper than Slack, which makes sense if Workplace wants to grab users from other platforms.

Some good (and bad) points:

  • Workplace accounts are different from Facebook accounts. That’s good; separating work and play means better privacy overall.
  • Workplace has a Trust Center posted, like Office 365: Workplace Trust Principles. Good for you guys!
  • Workplace debuts with a handicap though—Facebook’s dubious privacy practices. It’s a separate system, but Workplace does run off Facebook’s servers. Some businesses will shy away on reputation alone (and I can’t honestly blame them).

I requested a trial. Curiously, I was prompted to select a time for a Live Demo, instead of a download link or registration page. Which gave me a nice overview of the platform before sending me a link to my new Workplace. After playing with it for a few days (and bugging my co-workers with random “Just testing!” calls), I think it’s time for my review.

So what kind of experience does Workplace give us? Is a “Facebook for Work” app what we need? What kind of pricing are we getting? Features? Let’s find out!

The Basics: Feature Sets

Skype for Business Workplace By FB
Instant Messaging Work Chat (Messenger on Steroids)
Voice Calls Voice Calls within Work Chat
Video Calls Video Calls within Work Chat
Conferences/Online Meetings Conferencing
Federation Multi-Company Groups
Presence Status  Presence Indicator
Response Groups Groups
Persistent Chat Work Chat
Runs On-Prem (Server)
or SaaS Option  (Office 365)
Runs as Cloud Service
with Mobile Apps


Workplace setup assistance
A Workplace post to help you with setup.

Before we get into the details on similarities & differences though, there’s an elephant in the (chat) room. Privacy.

The Privacy Question

Workplace does come from Facebook. And Facebook is famous for its, shall we say, cavalier attitude about user privacy.

You Should Go Check Facebook’s New Privacy Settings – WIRED (06-02-16)

The question is, does Workplace protect users’ privacy? As a business product, it does have a legal obligation. So far, I’ve seen no indication that it will gamble with user privacy. But given its creator, we must still wonder.

In the Workplace FAQs, we find several questions devoted to privacy and confidentiality. Like this one.

Who owns the information that employees create?
Like other cloud-based enterprise software, the employer does.

Pretty straightforward answer. Only time will tell what changes may appear in Workplace’s approach to privacy. As well as what the market believes about Workplace privacy.

The Similarities: Features, Familiar UI

In terms of features, both platforms are very similar. Workplace’s Work Chat mirrors Skype4B’s Instant Messaging. From there, you can add voice, video, or other people with a few clicks. Just like in Skype for Business.

I was able to test the calling function, but not video (think my cam’s broken). Calls in Workplace came through as clear as any Skype for Business call.

Familiarity is a big factor in both platforms. Workplace feels & acts almost identically to Facebook. Skype for Business feels & acts a lot like Skype (in some respects!). I must credit both Facebook and Microsoft on this. Familiarity is a big part of good user experience—it helps adoption, shortens the learning curve, and improves overall satisfaction.

Workplace by Facebook screen
Looks like Facebook. Is actually Workplace.

As you can see from the screenshot, Workplace’s interface is feed-based. Skype for Business’ interface is contact-based. So long as the user knows where to go for communications, the interface works. In this respect, Workplace has a leg up over other chat competitors, like Slack and HipChat.

The Differences: Pricing, On-Prem vs. Cloud, Apps

The biggest difference I see (at least right now) is that Workplace is cloud-only. No local deployment option exists. Not surprising, but for those who prefer deploying servers on-prem…Workplace is a no-go.

The pricing difference stems from this same disparity.

Workplace charges only by active users. Skype for Business Online does something similar through Office 365 user accounts. But Skype for Business Server does not. The server pricing is up-front, in the form of licenses and implementation costs.
Workplace just turns on and charges you for X users each month.

Their price point is lower than Microsoft’s Office 365. In fact, even considering Slack’s pricing, Workplace is the cheapest per month:

  • Office 365 Business plans run from $5/user/month to $12.50/user/month. The Enterprise plans run from $8/user/month to $35/user/month.
  • Slack charges $8/user/month for Standard, and $15/user/month for Plus.
  • Workplace starts at $3/user/month for the first 1,000 users ($2/user for the next 1,000, and $1/user after that).

Seems pretty obvious that Facebook wants to compete on price as well as features. Using such a low per-user pricing model is an attempt to leapfrog both Slack and Microsoft. Like its other platforms, the company may aim to grow Workplace at break-even (or even at a small loss) until it reaches juggernaut status. Then they can raise prices all they want.

It’s worked for them before; I must admit that. But only time will tell us if this pays off for Workplace’s adoption.

Finally, Workplace features third-party app integration. Facebook learned from its ecosystem of consumer apps & games, and built an API that will let developers build add-ons for Workplace too.

Apps & Permissions – Workplace Docs

You can do this with Skype for Business as well, to some degree. There are many third-party apps which extend the Skype for Business system. (We’ve reviewed a few here on the blog – search around!)

Microsoft even maintains a registry: Skype for Business Apps, though it is incomplete. In terms of third-party integration, Workplace has a bit of an edge here. Like Slack, it appears designed to work with other apps from the start.

Final Words: Workplace Has the Chops, But Will Businesses Bite?

Facebook is moving into an already-populated space, where competitors have had years to build up their audiences, and trying to take it over. Nothing inherently wrong with such a practice—disruption feeds innovation.

But I can’t help thinking Workplace will never get out from under Facebook’s privacy question. If there’s a data leak, or Workplace data “accidentally” shows up in Facebook ad deployments? Then Workplace is DOA…and thousands of businesses are in serious trouble.

A final note: Workplace is still the new kid on the block. I will revisit this topic again later, after the market’s had time to chew through Workplace more, and we see what kind of management path Facebook takes with it.

Which do you prefer using—Workplace by FB or Skype for Business? Are there situations where you prefer one over the other?  Please comment or email me what you think.


How to Resolve a Communication Issue Between Skype4B Online and Skype4B Server

Back again, with a reader comment about communication issues. The other day, Marcos commented:

“Is there an incompatibility issue when establishing communication between organizations using SFB Online vs on Premise? We are using Online, however we cannot reach contacts outside our organization that use on Premise.
Is there any additional set up needed on each side?”

Yes, there is. Skype for Business Online and Skype for Business Server can (and should) communicate between one another. But you do need additional setup to connect them. I don’t know how much configuration Marcos did, but for sake of completion, I’ll proceed as if no configuration has taken place.

Communications between a Skype for Business Server, and Skype for Business Online, are what Microsoft calls “business-to-business communication.” To enable it, you’ll have to do three things.

  1. Enable business-to-business communication for users in the Office 365 Admin Center (Skype for Business Online)
  2. Configure federation with Skype for Business Online (on-premise Skype for Business Server)
  3. Update firewall settings (both ends)
Office Chats
“Can you hear me?” “I can’t hear anything.”  “Are you muted?”

How to Enable Business-to-Business Communication in Office 365 Admin Center

(Please note: You’ll need Office 365 Admin privileges to make this change.)

  1. Sign in with your Office 365 admin account at
  2. In the Office 365 admin center, go to Admin Centers > Skype for Business.
  3. In the Skype for Business admin center, select Organization > External Communications.
  4. To set up communication with a specific business or with users in another domain, in the drop down box, choose “On only for allowed domains.”
    • If you want to enable communication with everyone instead, choose “On except for blocked domains.”
  5. Under Blocked or Allowed Domains, click the +. Add the name of the domain(s) you want to allow.
  6. If the domain you want to enable is another Office 365 account, make sure their admin repeats the above steps, entering your domain.
  7. If you’re using the Windows Firewall, Skype for Business opens the required ports automatically.  If not, see “Firewall Settings” below.
  8. Wait up to 24 hours before testing. (That’s how long it can take to populate changes across all the Office 365 datacenters.)

More information available here: Allow users to contact external Skype for Business users – Office Support

How to Configure Federation with Skype for Business Online

Unsurprisingly, you use federation to enable on-premise communication with Skype for Business Online. However, we will also have to make a change in Office 365 Admin for this too.

Step 1: Set Federation for Skype for Business Online on Edge Server. All we need here are two cmdlets, entered in Skype for Business’ Management Shell.

Set-CSAccessEdgeConfiguration -AllowOutsideUsers 1 -AllowFederatedUsers 1 -EnablePartnerDiscovery 1 -UseDnsSrvRouting

New-CSHostingProvider -Identity SkypeforBusinessOnline -ProxyFqdn “” -Enabled $true -EnabledSharedAddressSpace $true -HostsOCSUsers $true -VerificationLevel UseSourceVerification -IsLocal $false -AutodiscoverUrl

Step 2: Configure Skype for Business Online for a Shared SIP Address Space.  This step is more complicated. You’ll have to establish a remote session with the Skype for Business Online tenant, from your on-premise Skype for Business Server.

How? With this: Skype for Business Online, Windows PowerShell Module

You’ll need to download & install the module on your server. Then, you can establish the remote session by entering these cmdlets:

Import-Module SkypeOnlineConnector
$cred = Get-Credential
$CSSession = New-CsOnlineSession -Credential $cred
Import-PSSession $CSSession -AllowClobber

Okay! All that work to establish a remote session.   Step 3:  Enter Configuration Cmdlet.  Just enter this cmdlet:

Set-CsTenantFederationConfiguration -SharedSipAddressSpace $true

That’s all.

More information available here: Configure federation with Skype for Business Online – TechNet

Firewall Settings

If you’ve configured both Skype for Business systems, but still receive error messages when communicating, chances are you need to update your firewall.

First, make sure your firewall allows client computers to access the following FQDNs:

  • *
  • *

Double-check that all necessary ports are open, regardless of which service you’re using. We often run into Skype4B Server deployments where the internal video ports (50020 to 50039 UDP and TCP) are open. But some of the external video ports were not–3478 UDP in particular. (Total external video ports are 443 TCP, 3478 UDP, & 50000 to 59999 UDP and TCP.)

If more advanced configuration is needed, here’s a list of Office 365 URLs and IPs. It should identify the pertinent information needed to update your firewall settings.
Office 365 URLs and IP Address Ranges – Office Support

Here’s the same list, for Skype for Business Server’s Edge Server.
Edge Server environmental requirements in Skype for Business Server 2015 – TechNet

Communication Established. Proceed with Work.

Once federation is set up between the two services, your users should be able to chat, call, have video chats, whatever they like.

Marcos, I hope this helps you out!  As well as any other reader who’s having trouble with communications between Skype for Business Server and Skype for Business Online.

(If that’s you, or you have a similar issue going on, please comment or email your experience. We try to help whenever possible!)

Next time, we resume our VS. comparisons, with the newer collaboration platforms mentioned in The Security Behind 6 Business Chat Apps (Including Skype for Business).  Join us then!