Mastering skype for business 2015

Wow, what a journey from the days of Lync Server 2010, when Nathan Winters asked me to co‐author our Mastering Lync Server 2010, through the next release and now to Mastering Skype for B

Mastering

Skype® for

Business 2015

Mastering

Skype® for

Business 2015Keith Hanna

Development Editor: Alexa Murphy

Technical Editor: Martin Rinas

Production Editor: Christine O’Connor

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10 9 8 7 6 5 4 3 2 1

book but always) I promise you don’t have to remind me anymore To my daughter, Rosie, for always being right, and to my son, Jamie, who also teaches patience We still make a great team!

Wow, what a journey from the days of Lync Server 2010, when Nathan Winters asked me to

co‐author our Mastering Lync Server 2010, through the next release and now to Mastering Skype for Business 2015 on my own Nathan’s role has changed to focus more on the cloud, so, sadly, he wasn’t able to contribute as much to this one as with the previous books

Thank you to the many readers of the Lync books who have gotten in touch either via email

or direct meetings at conferences and user groups and to the other customers—without your feedback and ongoing support, I wouldn’t have gotten to book 3! Keep the feedback coming (even the bad constructive stuff!)

Throughout the process, I have been supported, guided, and mostly cajoled by the great team at Sybex Several of the original editors have moved on in the five‐year journey to this edition but have been ably replaced by Ken Brown, Grace Davis, Alexa Murphy, and Christine O’Connor All have been responsible in some way to take the scrawls that I have pulled together and turn them into something readable Any errors are certainly not their fault There are many more nameless (to me at least) people at Sybex working behind the scenes, who also deserve thanking

Speaking of which, no technical book can be released without thorough cross‐checking, and for that I am extremely thankful to Martin Rinas, our technical editor, who spent many hours going through the material and replicating the examples to ensure technical accuracy In the past I’ve been the one correcting him, but things have certainly swapped around now

Some vendors have provided test devices and support and in some cases have contributed directly to chapters with content Thanks to the following:

Actiance: Robin Smith

Kemp: Barghav Shukla

MindLink: Howard Travers, Annekathrin Hase, Dalia Valkiunaite

Sennheiser: Charlotte Gaskin, Steve Bailey

Snom: Lesley Hansen, Alison Tetlow, Hoang‐Hoa Nguyen

My thanks go to all involved in helping to create this book

My advice to others: For anyone interested in learning more about or swapping UC war stories (or even those who just fancy a beer), join your local UC user group These groups are invaluable resources both for learning and for networking Catch up with these people; they don’t bite!

Keith Hanna started university life at Sheffield University ing software engineering but finished by graduating from Queen’s University, Belfast, in computer science His first “real” job was with Lucas Aerospace as a software developer working on aircraft engine control systems—it wasn’t rocket science, but it was close! Moving to England from Ireland, Keith helped to design and deploy a commu-nications system for the emergency services, but found his calling in Windows‐based application design and support, eventually making his way to Microsoft, where he stayed for eight years, working in a number of roles from engineer to consultant to architect He left in November 2014 to start a two‐year study period for an MBA, while picking up small pieces of Skype for Business consultancy and training work.

study-Keith has contributed several articles to TechNet as well as several chapters in the Lync 2010 Resource Kit He has written training courses for OCS R2 and Lync, as well as exam questions

He is a Microsoft Certified Master He’s not aware of any life outside work, and he will be keen

to discover if such a thing exists now that the book is finished, although it didn’t really happen after the previous one

Introduction xxiii

Part 1 • Fundamentals    1

Chapter 1 • What’s in Skype for Business?  3

Chapter 2 • Standards and Protocols  37

Chapter 3 • Security  73

Chapter 4 • Desktop Clients  111

Chapter 5 • Mobile Devices  145

Chapter 6 • Devices 163

Part 2 • Getting Skype for Business Up and Running 201

Chapter 7 • Planning Your Deployment 203

Chapter 8 • Installation 239

Chapter 9 • Migration and Upgrades 291

Chapter 10 • Online and Hybrid 307

Part 3 • Administration 337

Chapter 11 • Role-Based Access Control  339

Chapter 12 • User Administration  367

Chapter 13 • Archiving and Monitoring  405

Chapter 14 • Planning for Adoption  449

Chapter 15 • Troubleshooting  461

Part 4 • Voice 489

Chapter 16 • Getting Started with Voice  491

Chapter 17 • Call Admission Control 527

Chapter 18 • E9-1-1 and Location Information Services  567

Part 5 • Other Dependent infrastructure 587

Chapter 19 • Extended Voice Functionality  589

Chapter 20 • SQL Server  639

Chapter 21 • Reverse Proxies, Load Balancers, and Gateways  673

Chapter 22 • Exchange, SharePoint, and Office Web Application Server 705

Chapter 23 • Skype for Business 2015 Development  763

Appendices 777

Appendix A • The Bottom Line 779

Appendix B • Introduction to PowerShell, the Skype for Business Management Shell, and Regular Expressions 809

Appendix C • Using Persistent Chat Effectively 851

Index 865

Introduction xxiii

Part 1 • Fundamentals 1

Chapter 1 • What’s in Skype for Business? 3

Understanding the Skype for Business Client 3

Connecting via the Skype for Business 2016 Client 4

Communicating via the Client 9

Collaborating via the Client 13

Understanding Skype for Business Server 2015 15

Managing Skype for Business Server 2015 16

Understanding the Voice Capabilities 29

Understanding the Unified Communications Managed API Capabilities 33

Unwrapping the SDK 33

The Bottom Line 34

Chapter 2 • Standards and Protocols .37

Understanding SIP’s Origins 37

Circuit-Switched Networks 37

Packet-Switched Networks 42

The Session Initiation Protocol in Depth 50

Using SIP 51

SIP Protocol Formatting 54

Providing Presence 57

Sending an Instant Message 57

Understanding Skype for Business Codecs and Standards 59

The Bottom Line 71

Chapter 3 • Security 73

Securing External Access 74

Edge Security Components 74

Understanding Core Security 92

Media and Signaling Security 92

Authentication 93

Certificates 97

Providing Security Administratively 98

Client-Version Filtering 98

Message Hygiene 103

Configuring Antivirus Scanning 106

Disclaimers 107

PIN Policy 108

Federation and How to Control It 108

The Bottom Line 109

Chapter 4 • Desktop Clients 111

User Clients 111

Skype for Business 111

Web App 121

Windows Store App 125

Skype for Business 2016 Basic 125

Client Configuration 126

Discovery and Connection 128

Persistent Chat Client 129

Creating a Chat Room 135

Conferencing Clients 138

Virtualized Clients 140

Legacy Clients 142

The Bottom Line 143

Chapter 5 • Mobile Devices 145

Mobile Client Capability 145

Managing Mobile Clients 154

Deploying and Configuring Mobility on Skype for Business Server 2015 156

Configuring for Mobile Access 156

Confirming the Mobility Service 158

How Does Mobility Work? 158

How Does Presence Work? 160

The Bottom Line 162

Chapter 6 • Devices 163

USB Devices 163

Headsets 165

Handsets 168

Personal Speakerphones 169

IP Desk Phones 170

Phone Edition 170

3PIP 185

Better Together over Ethernet 193

Meeting Room Devices 193

Video Endpoints 195

Integrating with Hardware Video Conferencing Platforms 196

Configuring Lync and HDX Integration 197

The Bottom Line 199

Part 2 • Getting Skype for Business Up and Running 201

Chapter 7 • Planning Your Deployment 203

Capturing the Requirements 203

Understanding What Is Wanted 204

Understanding What Is Currently in Place 205

Understanding the Basics 205

Using the Capacity Planning Toolset 207

Defining a Topology with the Planning Tool 208

The Stress and Performance Tool 221

Bandwidth Calculator 230

Installation Prerequisites 232

Recommended Hardware 232

Software Prerequisites 233

Disaster Recovery 236

The Bottom Line 238

Chapter 8 • Installation 239

Getting Up and Running with Skype for Business 240

Preparing Active Directory 240

Topology Builder 246

Configuring Windows Server 2012 252

Installing the Standard Edition Server 258

Completing Post-deployment Tasks 266

Basic Administrative Permissions 266

Testing the Installation 267

Kerberos Authentication Configuration 269

Configuring External Access 271

Installing the Director 272

Installing the Edge Server 276

Executing Enterprise Deployments 282

Working in Large Active Directories 282

Delegating Setup Permissions 284

Installing Enterprise Pools 284

Installing Persistent Chat 287

Considerations for Branches 288

Automating Installation Using PowerShell 289

The Bottom Line 289

Chapter 9 • Migration and Upgrades 291

Understanding Migration 291

Coexistence 292

Considering Client Pain Points 293

Policies 293

The Client Experience 294

Migrating to Skype for Business 297

Deploying the First Skype for Business Pool 298

Upgrading to Skype for Business 299

Third-Party Applications 305

Client Rollout 305

The Bottom Line 305

Chapter 10 • Online and Hybrid 307

Putting Skype for Business Online in Context 307

Understanding Hybrid Voice and Cloud PBX 308

Hybrid Voice 308

Cloud PBX 310

Voice Mail 311

Configuring for Office 365 311

Configuring Skype for Business Online for Hybrid 312

Configuration for Hybrid 313

Sign-in/Registration Process 319

Call Flow Scenarios 321

E9-1-1 and Media Bypass 327

Conferencing 328

Implementing Cloud PBX 329

Cloud PSTN Calling 330

On-Premise PSTN Calling 330

Migrating to Hosted Voicemail 331

Configuring Office 365 Dial Plans 331

Configuring On-Premise Skype for Business 334

The Bottom Line 335

Part 3 • Administration 337

Chapter 11 • Role-Based Access Control 339

Introducing RBAC 339

Roles and Scopes 340

Skype for Business Roles and PowerShell 341

Understanding the Standard Roles 346

CSAdministrator 348

CSUserAdministrator 349

CSServerAdministrator 349

CSViewOnlyAdministrator 349

CSArchivingAdministrator 350

CSHelpDesk 350

CSVoiceAdministrator 350

CSResponseGroupAdministrator 351

CSResponseGroupManager 351

CSLocationAdministrator 351

CsPersistentChatAdministrator 351

Creating New Roles 352

Planning Combinations 352

Creating the Role 356

Manipulating Roles 359

Assigning and Removing Roles 359

Deleting Roles 359

Filtering Specific Roles 360

Adding and Removing Cmdlets or Scripts from Roles 360

Reporting on Roles 362

The Bottom Line 364

Chapter 12 • User Administration 367

User Configuration Basics 367

Enabling and Disabling 374

Making Changes to Users 377

Understanding Skype for Business Policies 381

In-Band Provisioning 381

Understanding Where Policies Apply 382

What About Group Policy? 383

Manipulating Policies 385

Viewing Policies 385

Creating and Assigning Policies 389

Editing Existing Policies 394

Removing or Resetting Policies 395

Choosing the Right Policy for the Job 397

ClientPolicy 400

ClientVersionPolicy 401

ClientVersionConfiguration 401

PrivacyConfiguration 401

PresencePolicy 402

CsCallViaWorkPolicy 402

CsThirdPartyVideoSystemPolicy 402

UserServicesConfiguration 402

The Bottom Line 403

Chapter 13 • Archiving and Monitoring 405

Deploying the Architecture 405

Prerequisites 406

Installation 406

Database Support, Architecture, and Capacity 407

High Availability 407

Configuring Policies 408

Deploying the Reporting Pack 411

Interpreting the Monitoring Server Reports 414

Understanding Voice Quality 415

MOS Values by Codec 416

Viewing the Reports 417

System Usage Reports 419

Monitoring Service with the Management Pack 432

Deploying Synthetic Transactions with SCOM 438

Using Statistics Manager 443

The Bottom Line 448

Chapter 14 • Planning for Adoption  449

Understanding the Power of UC 449

The Promise 450

The Pitfalls 450

Introducing Skype for Business to Your Business 451

Piloting Skype for Business 452

Training Your Users 454

The Bottom Line 459

Chapter 15 • Troubleshooting  461

Covering the Basics 461

Confirming a Network Connection 462

Confirming Secure Connectivity 465

Checking for Audio/Video Peer-to-Peer Connectivity 465

Using Logging to Identify Problems 472

Using Centralized Logging 473

Making Logging Easier 476

Using Snooper.exe 476

Diagnostic Message Text 480

Advanced Troubleshooting Methods 480

Investigating Web Components 480

Performance Counters 481

Synthetic Transactions 483

Monitoring Reports 485

Client Side 486

The Bottom Line 487

Part 4 • Voice 489

Chapter 16 • Getting Started with Voice  491

The Backstory 491

Understanding the Voice Capabilities 492

Private Line 495

Malicious Call Trace 497

Media Bypass 499

Understanding the Voice Architecture 500

Understanding Mediation Servers 502

High Availability and Resiliency for Voice 503

Configuring Enterprise Voice 513

Configuring the Client Enterprise Voice Options 514

Configuring the Server Enterprise Voice Options 523

The Bottom Line 525

Chapter 17 • Call Admission Control 527

Understanding Call Admission Control 527

How Call Admission Control Works 529

Where Call Admission Control Works 532

Underlying Network Requirements 534

Designing for Call Admission Control 541

Configuring Call Admission Control 549

Configuring the Global Setting 550

Defining the Policy Profile Settings 551

Defining Regions 552

Defining Sites 554

Defining Subnets 557

Defining Region Links 558

Assigning Region Routes 560

Assigning Policies 561

Identifying Calls on a Network 563

Reporting on Call Admission Control 564

The Bottom Line 564

Chapter 18 • E9-1-1 and Location Information Services  567

Understanding E9-1-1 567

Current Legislation 570

Configuring E9-1-1 570

Configuring PSTN Usage 571

Configuring Location Policies 571

Defining the SIP Trunk 575

Configuring the Voice Route 575

Configuring Location Information 576

Configuring the Location Database 576

Using Secondary Location Databases 581

Retrieving the Location Data by a Client 581

Roaming Users 583

Placing a Call 584

Testing an E9-1-1 Call 585

The Bottom Line 586

Part 5 • Other Dependent Infrastructure 587

Chapter 19 • Extended Voice Functionality  589

Setting Up Dial-in Conferencing 589

Understanding Dial-in Conferencing 590

Configuring Dial-in Conferencing Features 592

Implementing Dial-in Conferencing 601Using Dial-in Conferencing 603Defining Response Groups 607Understanding Response Groups 607Implementing Response Groups 616Using Response Groups 620Understanding Call Park 622Setting Call Park Options 623Implementing Call Park 627Using Call Park 628Configuring Unassigned Numbers 631Using Unassigned Numbers 631Implementing Unassigned Numbers 635The Bottom Line 637

Chapter 20 • SQL Server  639

Versions of SQL Server 639Installing SQL Server Express 641Installing a SQL Server Stand-Alone or Clustered Server 643Installing a Mirrored SQL Server Pair 646Installing AlwaysOn Availability Groups 655Migrating SQL Server Databases to AlwaysOn Availability Groups 664Updating SQL Server Databases 666SQL Server Databases and Permissions 667The Bottom Line 670

Chapter 21 • Reverse Proxies, Load Balancers, and Gateways  673

Configuring Load Balancers 673Load Balancing the Front End and Director Pools 674Load Balancing Office Web Apps Server Farms 679Load Balancing Edge 681Configure a Load Balancer for the Web Conferencing Edge Interface 683Configure a Load Balancer for the A/V Edge Interface 683Configure a Load Balancer for the Internal Edge Interfaces 684Implementing Reverse Proxies 684Configure a Reverse Proxy/Load Balancer for External Web Services 686Understanding Gateways 688Public Switched Telephone Network 689Internet Telephony Service Provider 690Private Branch Exchange 692Achieving Connectivity 693SIP address and ISDN Gateways 694Integrating with Your PBX 698Integration Options 699The Bottom Line 703

Chapter 22 • Exchange, SharePoint, and Office Web

Application Server 705

Integrating Skype for Business with Exchange 705Configuring Exchange Integration Prerequisites 707The Voice Mail Platform for Skype for Business 715Free/Busy, and Other Integration 730Outlook Web App Integration 731Understanding and Configuring the Unified Contact Store 738Integrating into Exchange for Compliance Archiving 741Using High-Resolution Photos in Skype for Business 746Integrating Skype for Business with SharePoint 749

IM and Presence Within Sites 749Skill Search 750Photos 754Converting Recorded Meetings into SharePoint Asset Libraries 756Business Process Communication Workflows 757Integrating Skype for Business Server with Office Web Application Server 758The Bottom Line 761

Chapter 23 • Skype for Business 2015 Development  763

Understanding Development Options 763Unified Communications Managed API 5.0 764Software Defined Networking 765Microsoft SIP Processing Language 767Skype for Business 2015 API 770Unified Communications Web 2.0 771Configuring the Infrastructure 772Configure a Trusted Application Server/Pool 773Configure a Trusted Application 774Configure a Trusted Application Endpoint 774The Bottom Line 775

This book is the third in the Sybex Mastering series on the subject of Microsoft’s Unified

Communications (UC) platform With the release of Skype for Business, we are into the fifth generation of a platform that provides a comprehensive set of functionality, which has continu-ally placed it in the top right of the Gartner Magic Quadrant for UC

Skype for Business is a new name for the platform, which while clearing things up causes

an equal amount of confusion For the last several years, I have been trying to explain to people what I do, and in speaking with others working with these products, the conversation is famil-iar, along the lines of this:

Me: “Hi, how are you?”

Other: “Good, thanks So, what is it you do?”

Me: “I work in IT.” (Often this will end the conversation!)

Other: “Oh, really what specifically?”

Me: “Lync.”

Other: <blank stare> “Oh, never heard of it.”

Me: “Have you heard of Skype?”

Other: “Yes.”

Me: “Well, think of it as Skype, but for businesses.”

Other: “Ah.”

Now Microsoft has made our lives slightly easier with the name change, but of course there

is always the risk that businesses think they don’t need any help to implement it Skype just works, right?

While Skype for Business brings a new name and interface to Lync, you’ll see a lot of the functionality remains similar if not identical Under its new leadership, Microsoft is changing the way products are developed, released, and paid for This has an impact in that the products evolve quickly over short periods of time—even in the time taken to write this book (around seven months from beginning to end) there have been updates Traditionally these would have been patches to fix bugs; however, now they are being used to deploy new functionality

With this in mind, I set out to reinforce any prior knowledge you might have of the server platform but not to assume any and thereby take you on a journey from the key fundamentals of Skype for Business all the way through deployment and how best to integrate with third-party systems All of this is based on the release-to-manufacture (RTM) code

I have attempted to ensure that you can gain insight into real-world environments both through the use of lab systems that represent those that might be found in an enterprise net-work and through the use of real-world case studies that highlight examples of day-to-day expe-rience as a consultant to some of the world’s largest organizations

What You Need to Run Skype for Business Server 2015

As you read this book, you will find that there are a range of components that all come together

to make Skype for Business function These include the Skype for Business Server software, the Skype for Business client, and the supporting technology from Microsoft Windows Server 2012 R2 and Microsoft SQL Server 2014 Of course, there are additional pieces that can be integrated, such as gateway devices, telephone devices, and software components such as Exchange and SharePoint

With this much complexity, you may be wondering how on Earth you are going to be able

to get started with learning In addition to all the components, you will find when looking at the published minimum system requirements for Skype for Business that the main Front End (or Standard Edition) servers require a minimum of 16GB of RAM and eight CPU cores alone I cover all this in depth in Chapter 7, but no doubt you will think that is rather a challenge for a lab Well, don’t worry! It is perfectly possible to set up a capable lab system on a single machine

In fact, while writing this book, I ran the numerous lab systems on a variety of hardware, ing from laptops with 16GB of RAM and a pair of fast hard drives for the virtual machines to large workstation hardware with 64GB and six hard drives All in all, this is equipment that is well within the reach of any enterprise looking to get up to speed with Skype for Business and something that anyone studying IT as they learn for their career can get hold of for not ridicu-lous sums

rang-Within the constraints of the hardware mentioned, I created the labs using Microsoft Hyper-V technology to virtualize many machines The labs ranged from two machines cover-ing a domain controller and a single Skype for Business server all the way up to the migration lab, which had both Lync and Skype for Business installed with full external communication and mediation servers for connectivity to the PSTN, where I was running 20 servers on a single piece of hardware So while for production use you must take care to size things according to best practice, in the lab you can learn a great deal with a single server, Hyper-V, some public

IP addresses, public certificates, and a SIP trunk—which are all readily available for affordable amounts of money

What’s Inside

This book is arranged in five main sections, which focus on key elements that help build your knowledge of Skype for Business, starting with fundamentals that get you up to speed You will then move on to getting your first Skype for Business system up and running through to admin-istrating your system At that point, the book takes a deep look into using Skype for Business

as your telephony platform, before moving on to cover how to integrate Skype for Business into other systems

When first picking up a new book, people frequently jump straight to a chapter that answers some immediate need or interest I have attempted to build concepts throughout this book, with most of the later chapters assuming you are familiar with the previous material I have, of course, referenced that earlier material wherever possible in case you need to brush up, but as a general recommendation, if you’re new to Skype for Business, you will have the most success by reading through the chapters in order

Part I: Fundamentals

This section covers the background information that will help you understand what makes

Skype for Business tick

Chapter 1: What’s in Skype for Business 2015? This chapter runs through Skype for

Business from top to bottom, covering key concepts, features, and where Skype for Business sits in the history of real-time communication products from Microsoft

Chapter 2: Standards and Protocols Like any technical product, Skype for Business is

underpinned by numerous protocols and standards that enable it to operate and interoperate with other platforms This chapter focuses in particular on SIP, which enables the majority of Skype for Business communications

Chapter 3: Security Security is front of mind for all administrators these days This chapter outlines the threats to Skype for Business and explains its architecture in a security-focused manner that will enable you to discuss requirements with your security team Also covered are some of the administrative practices needed to help you administrate Skype for Business securely

Chapter 4: Desktop Clients Without clients, any server product would be pretty useless! In this chapter, you’ll look at the clients available on a PC, Mac, and browser, and then you’ll do

a dive deep into how the clients connect to Skype for Business infrastructure

Chapter 5: Mobile Clients Mobility has become a much more significant usage case in

recent years, and in this chapter, you will look at the clients available on a Windows Phone and iOS devices (Android clients will be available by the time you read this) and dive deeper into how the mobile clients connect to Skype for Business infrastructure

Chapter 6: Devices This chapter wraps up the client connectivity methods by looking at specifically manufactured devices for connectivity for telephony and/or conferencing, cover-ing the clients that run Skype for Business directly as well as non-Skype for Business clients that can integrate

Part II: Getting Skype for Business Up and Running

This part is where you actually get hands-on It covers planning and sizing and then both the installation and upgrade processes

Chapter 7: Planning Your Deployment While you’re probably all keen to dive in and start playing with the nuts and bolts, planning is essential to ensure you achieve what is required This chapter shows you how to plan utilizing the available tools, and it helps you understand the Skype for Business prerequisites, enabling you to choose which hardware to use and

whether virtualization will work for you

Chapter 8: Installation By the end of this chapter, you should have installed your first tem This chapter covers preparing your underlying server OS through publishing Skype for Business to the Internet, with all the steps in between!

sys-Chapter 9: Migration and Upgrades Skype for Business is the latest in a line of real-time communications products from Microsoft This chapter shows you how to get from the ear-lier Lync Server products to Skype for Business

Chapter 10: Online and Hybrid The “cloud” is becoming more dominant in everyday puting, and Microsoft is driving cloud adoption specifically through Office 365 Skype for Business is included in the Office 365 product suite, and through this offering you can join an on-premises solution to the cloud solution, creating a hybrid This chapter walks through the requirements to do so, as well as discusses the features There will be more available by the time you read this!

com-Part III: Administration

Having planned and installed Skype for Business in the previous section, this part moves on to cover administration These chapters cover role-based access, explain admin roles and policies, and even cover troubleshooting

Chapter 11: Role-Based Access Control Role-Based Access Control (RBAC) changes the granularity and ease with which an administrator can be granted permissions required for their job and only their job, allowing specific delegation of functionality to groups of people This chapter shows you how Skype for Business implements RBAC and how to use it to implement secure administration of Skype for Business

Chapter 12: User Administration This chapter shows how to manage users, enabling, abling, and configuring them both individually and through policies and to use the Skype for Business features they require

dis-Chapter 13: Archiving and Monitoring Skype for Business enables communication, and

in many organizations communications must be archived This chapter covers how this is achieved with the Archiving role, as well as options to allow Exchange to archive the data It also covers the way in which you can inspect the communication passing through Skype for Business, not only for quality but also more traditionally, showing who spoke with whom Finally, the chapter also covers how to monitor the Skype for Business service as a whole using System Center Operations Manager (SCOM)

Chapter 14: Planning for Adoption While this book has focused on the technology that is Skype for Business, there is another major aspect to utilizing Skype for Business: how do you get Skype for Business adopted in your organization? Without a proper plan and a great team that includes people ranging from senior personnel to those using the technology every day, you may not have great success deploying Skype for Business This chapter discusses some

of the key elements that come together to enable a business to successfully adopt Skype for Business

Chapter 15: Troubleshooting As with any system, there will be times where things don’t work as they should This chapter works through key troubleshooting concepts and then looks at the tools available in Skype for Business, or available separately as downloads, and how to use them when trouble strikes

Part Iv: voice

Skype for Business builds on the vision of Lync Server toward becoming a full-fledged phony system (PBX) This section focuses on using Skype for Business as your PBX, taking you from basic phone calls through to complex automated call distribution systems

tele-Chapter 16: Getting Started with Voice Skype for Business provides all the capability

needed to be a large enterprise telephony platform This chapter introduces you to the world

of the PBX It covers the features available in Skype for Business and the architecture that supports them

Chapter 17: Call Admission Control One of the biggest considerations when utilizing data networks for audio and video communication is bandwidth usage Call Admission Control enables you to map out your network and protect it from overuse This chapter shows you how to do this with Skype for Business

Chapter 18: E9-1-1 and Location Information Services Especially in North America, the ability to locate where a phone call is being made from and to provide that information to the emergency services is mandatory This chapter discusses how to provide this functionality with Skype for Business; it also shows how those outside of North America can use this inno-vative technology

Part v: Other Dependent Infrastructure

One of the huge benefits of Skype for Business being a software platform is that it is easy to

extend and integrate with other systems This part covers that extensibility, looking at the way Skype for Business integrates with both other Microsoft and non-Microsoft products

Chapter 19: Extended Voice Functionality Skype for Business can do far more than just basic phone calls This chapter looks at how to implement your own audio-conferencing

bridge, how to set up your own mini call center or help desk, and how to deal with other

voice scenarios, such as the need to park calls for others to pick up and to deal with calls to people who have left your company

Chapter 20: SQL SQL is the engine room that drives Skype for Business Every server has

at least one SQL Express installation locally, and it is critical to the ongoing operations In this chapter, you will see how to deploy and configure SQL to cater for high availability, as well

as moving from SQL mirroring to SQL AlwaysOn Availability Groups

Chapter 21: Reverse Proxies, Load Balancers, and Gateways These devices (or services) are the gateway to the outside world; reverse proxies are used for external client connectivity via the Internet, and gateways are used via the PSTN Load balancers are there to help with the high availability of the services This chapter looks at the features enabled and configura-tion requirements of these devices

Chapter 22: Exchange, SharePoint, and Office Web Application Server While Skype for Business contains a huge amount of technology, it is enhanced even further through tight integration with other Microsoft products This chapter covers the provision of voice mail and presence integration with Exchange, as well as presence integration and workflow with SharePoint It also covers how client PowerPoint content is presented via the Office Web

Application Server

Chapter 23: Skype for Business 2015 Development This chapter provides an overview of the development capabilities of Skype for Business, such as how you can leverage the infra-structure to integrate into existing line-of-business applications or create your own

xxvIII | IntroductIon

Appendixes

There are three appendixes The first covers all the learning points from throughout the book,

the second covers some basic PowerShell capability for those new to PowerShell, and the third

discusses Persistent Chat use cases

Appendix A: The Bottom Line Throughout the book, “The Bottom Line” section appears

at the end of each chapter It asks relevant questions to help test your understanding of the material in that chapter This appendix covers all those questions and includes the answers

so you can verify yours

Appendix B: Introduction to PowerShell, the Skype for Business Management Shell, and Regular Expressions PowerShell is what underpins the whole management inter-face of Skype for Business While most people are likely to be familiar with PowerShell (it’s been released for more than eight years now), it may be new to some In this chapter, you learn what PowerShell is, how to use it, and more importantly how to work with Skype for Business using PowerShell

Appendix C: Using Persistent Chat Effectively Persistent Chat is a difficult aspect of Skype for Business to understand and use well in organizations This chapter will showcase

a number of scenarios where it is used well and can bring value

The Mastering Series

The Mastering series from Sybex provides outstanding instruction for readers with intermediate

and advanced skills in the form of top-notch training and development for those already

work-ing in their field and clear, serious education for those aspirwork-ing to become pros Every Masterwork-ing

book includes the following:

◆ Real-World Scenarios, ranging from case studies to interviews that show how the tool, technique, or knowledge presented is applied in actual practice

◆ Skill-based instruction, with chapters organized around real tasks rather than abstract concepts or subjects

◆ Self-review test questions, so you can be certain you’re equipped to do the job right

Conventions Used in This Book

Before you set off into the world of Skype for Business described in this book, there is one final

piece of information you should know Throughout the book, we have used various methods to

describe things In particular, we have had many discussions about how best to refer to Skype

for Business After all, it’s much more of a mouthful than Lync

Aside from trying to shorten the name, Microsoft isn’t happy about using variations of S4B

or SfB Skype was an option, but this refers to the “consumer” brand of Skype The best I’ve

come up with is to use the following variations when referring to different aspects of Skype for

Business:

◆ Skype for Business Server 2015: This is the server product, in other words, the ture where you do the configuration

infrastruc-IntroductIon | xxIx

◆ Skype for Business 2016: This is the client, which users will use (Note the different

num-bering also.)

◆ Skype for Business 2015: This is also the client, but with the Lync 2013 client upgraded (see

Chapter 9, “Migrations and Upgrades,” for details)

◆ Skype for Business client: This primarily would be the Skype for Business 2016 client, but

it can also be more generic to include older clients such as the Lync clients that continue to

work

◆ Skype for Business Online: This is the Office 365 version of the Skype for Business product,

which is hosted and operated by Microsoft directly

◆ Skype for Business: This generically refers to all of the above, in other words, this

genera-tion of the product (previously called Lync)

In addition, when it comes to the management tools, there are two main interfaces: a

web-based control panel called Skype for Business Server Control Panel and a command-line shell

called the Skype for Business Server Management Shell, which is PowerShell based In the book,

I used the term PowerShell to describe the Skype for Business Server Management Shell.

Later versions of Windows Server (2012 +) are able to dynamically load the cmdlets from

other modules as needed, so there is no direct need to import the Skype for Business cmdlets;

simply start any PowerShell prompt and go However, on older versions of Windows, when

working with Skype for Business, unless explicitly stated otherwise, you should be using the

Skype for Business Server Management Shell

How to Contact the Author

I welcome feedback from you about this book Obviously, it’s always nice to get messages about

what you liked about the book, but I also welcome suggestions for improvements I could make

in future editions You can reach me at hannakeith@hotmail.com

Sybex strives to keep you supplied with the latest tools and information you need for your

work Please check its website at www.sybex.com/go/masteringskypeforbusiness, where I’ll

post additional content and updates that supplement this book should the need arise

Part 1

Fundamentals   

◆ Chapter 1: What’s in Skype for Business?

◆ Chapter 2: Standards and Protocols

◆ Chapter 3: Security

◆ Chapter 4: Desktop Clients

◆ Chapter 5: Mobile Clients

◆ Chapter 6: Devices

Chapter 1

What’s in Skype for Business? 

Skype for Business 2015 is the latest in the line of the Communications Server platforms from

Microsoft The platform originally started with Live Communications Server 2003 (some would

say with Exchange Conference Server 2000!) and continued through Live Communications

Server 2005, Office Communications Server (OCS) 2007, Office Communications Server 2007 R2,

and the two incarnations of Lync: Lync Server 2010 and Lync Server 2013

For those of you experienced with either version Lync Server (or indeed previous versions

of OCS/LCS), this chapter will call out some of the core capabilities introduced in previous

ver-sions as well as the new capabilities specific to Skype for Business, so some of this content may

be a refresher to knowledge you already have

In this chapter, you will learn to

◆ Describe the features of the client

◆ Describe the features of the server

◆ Describe the voice features

Understanding the Skype for Business Client

As an administrator, the first thing you’ll see is the Setup tool; however, the users will see the

client Therefore, understanding what the client can and will provide is important for

adminis-trators trying to sell the business justification It is also important in terms of what policies will

need to be configured to enable (or disable) features The Microsoft Unified Communications

family is so much more than a simple instant messaging (IM) tool or a phone, and treating it as

either end of the messaging scale will impact the way you deploy it to users At one end, the IM

capabilities can be deployed quite simply, whereas the phone integration will take significant

planning and should not be underestimated Some of the additional training capabilities freely

provided by Microsoft are covered in Chapter 14, “Planning for Adoption.”

With OCS (and to some extent LCS), the user experience was made up of a number of clients

◆ Communicator

◆ Live Meeting

◆ Group Chat

Lync 2010 consolidated the Communicator and Live Meeting clients into one; however, that

still left the Group Chat client as a separate installation requirement A number of large

finan-cial institutions that have a heavy reliance upon the Group Chat functionality have been asking

4 |ChaPter 1 What’s in skype for Business? 

for some time for the consolidation of this client Group Chat (now known as Persistent Chat)

was incorporated into the Communicator client in Lync 2013, so there’s only a single installation

required In addition, Persistent Chat is now a “full” function of Lync 2013 rather than a

down-load add-on as it was previously—more on this later

Chapter 5, “Mobile Clients,” covers in detail the mobility capability; this was first introduced with Cumulative Update 4 in Lync Server 2010 and has been expanded with each new iteration

of the product

With the Skype for Business branding, the client has had a facelift; new features introduced with Lync 2013, such as user photos, have been further improved, and other features have been

moved around to make them easier to find for users

In addition, device selection has been considered, with the clients being adapted to tablet devices as well as the expected mobile and desktop/laptop-style devices

The Communicator client is also now part of the Office suite and is no longer available rately Figure 1.1 shows the client when a user is first logged in

sepa-Figure 1.1

The client startup

screen

Connecting via the Skype for Business 2016 Client

To communicate and collaborate, Skype for Business client users need to be able to locate and

con-nect to each other on the network Over time, users will build their own contacts list (sometimes

called a buddy list); however, they need to find other users to be able to create and add to the list

The basic search functionality from previous versions has been retained and has been expanded

to include integration and key-skills searching within SharePoint as well as the expected Address

Book search Also available (introduced in Lync 2010) is the ability to remove the Address Book

download capability and provide only an online web-based search function Figure 1.2 shows the

client search bar and results window when data has been entered into the search bar

understanding the skype for Business Client | 5

Figure 1.2

The client search bar

and results window

From these results, you can initiate any type of communications modality The submenu is

opened by selecting the ellipsis (…)

To find more information from the user (the contact card), you have to at least appear to

begin a conversation with them Starting an IM conversation has the least impact in that until

you actually send a message, there is no prompt to the recipient Figure 1.3 shows the new-style

contact card, which you can see once you initiate communications and expand the user data

This information is captured from a combination of Skype for Business, Outlook, and Active

Directory attributes; if you don’t see information you’d expect to see, make sure the data is

avail-able in the source first!

Figure 1.3

The user contact card

6 |ChaPter 1 What’s in skype for Business? 

The User Properties box is extended to provide a lot more contextual information

◆ Department

◆ Office

◆ Phone numbers (work, mobile, home, if permitted)

◆ SharePoint links (to MySite, for example)

◆ Calendar information

◆ Location information (including local time and time zone)

This contact card provides a consistent client interface across all the integrated applications,

such as Office and SharePoint Connecting from other applications preserves context; if you start

a conversation from an Outlook email, both the subject and the priority are carried across to the

conversation windows and the document title is transferred from SharePoint The contact card

now includes the ability to provide location information, giving users a way to quickly establish

where people are currently, which can help them determine whether personal contact or a video

call is the more appropriate type of communication The location information also provides the

local time for the user, which can be extremely useful when people are spread across multiple

geographies

You can search across the following locations:

◆ Skype for Business contacts

◆ Active Directory

◆ Outlook contacts (including suggested contacts)

◆ The public Skype directory (optional, requires configuration)Introduced with Lync 2013, in conjunction with Exchange 2013, is the Unified Contact Store, where all contacts are merged and stored within the user mailbox (specifically within

the contacts folder) An additional capability introduced by the Unified Contact Store is the

ability to store high-definition (HD) photographs of the users In the past, photographs were

stored in SharePoint or Active Directory; now they are stored within the user mailbox in

Exchange 2013

Searching allows you to easily establish availability and identity (the extended contact card provides more information to help identify the correct recipient) and quickly establish contact

using any modality In addition to searching by name, the SharePoint integration allows you to

search by skills (or keywords) to help identify the correct person

As mentioned, the ability to add contacts (or buddies) and group them is retained; in

fact, it is expanded to include an auto-populated Frequent Contacts group This group is

automatically populated with your 10 most-frequent contacts, which are weighted based on

modality For example, someone you regularly call is going to be placed higher in the list

than someone you IM You’ll learn about other automatically created groups later in this

chapter

The Contacts tab, which is the default, contains a number of subtabs that provide different views (shown in Figure 1.4)

understanding the skype for Business Client | 7

Groups This is probably the most frequently used subtab; it is where you can find all the

contacts sorted alphabetically but also grouped together in user-defined groups

Status Under this subtab, all the contacts are sorted by availability, under the following

groups:

◆ Away (includes Off Work)

◆ Unknown

◆ Unavailable

◆ Online (includes Busy, In a Meeting, and Do Not Disturb)

Relationships Here, you can manage the permissions assigned to each contact The default

categories are as follows:

Friends and Family This relationship must be assigned manually It provides the

fol-lowing setting:

“Share all my contact information except meeting details.”

Workgroup This relationship must be assigned manually It provides the following

setting:

“Share all my contact information except Home and Other phone; contact can

inter-rupt Do Not Disturb status.”

Colleagues Any users from within the same Skype for Business organization (or Lync

if in coexistence) are automatically placed within this group and receive the following

setting:

“Share all my contact information except Home, Other, and Mobile phone, and

meet-ing details.”

External Contacts Any external (federated) users are placed within this group by

default and receive the following setting:

“Share only my name, title, email address, company, and picture.”

Figure 1.4

The groups subtab on

the Contacts tab

8 |ChaPter 1 What’s in skype for Business? 

Blocked Contacts This relationship must be manually assigned and provides the lowing setting:

fol-“Share only my name and email address; blocked contacts can’t reach me via Lync.”

Auto-Assign Relationship This item is not found in the Relationships tab; however, it can be found on a contact and is used to reset the privacy level

“Reset this privacy relationship to the default.”

New If users have added you to their contact list but you have not (yet) added them to yours, they will appear on the New tab

Add A Contact Provides a submenu with the following list of options for finding and ing a new contact:

add-◆ Add A Contact In My Organization

◆ Add A Contact Not In My Organization

◆ Create A New Group

◆ Display Options

Voicemail Display

The voicemail display within the skype for Business 2016 client is not as fully featured as the mail integration from within outlook skype for Business allows only basic integration, providing the name of the user (or phone number display, if caller id could not be matched to a contact), a play button, and the skype for Business interaction options allowing the call to be responded to from the client (using any modality)