Lync 2013 & Skype for Business side by side deployment

If an environment has an existing Lync deployment a number of options exist to introduce Skype for Business Server –

  • In place upgrade
  • Side by side deployment

In place upgrade provides a method to upgrade existing Lync 2013 servers so they become Skype for Business servers.  By doing so less work is required than a side by side deployment as no need exists to deploy a new environment from scratch.

Side by side deployment contains existing Lync 2013 environment and introduces Skype for Business Servers.  This method requires additional resources and time to deploy, migration of accounts and other items such as CMS, response groups, etc and then decommission the legacy environment.

This raises the question why would anyone want to do a side by side deployment when in place saves time?  There’s a number of reasons including

  • Risk adverse to upgrading production environment where failure could cause system disruption impacting staff.  You may have a single pool (or server) or you’re worried no pool pairing during the upgrade is too great a risk.
  • Existing deployment uses Windows Server 2008 R2.  Whilst in place upgrade will work with this server version it’s time to move on.
  • Existing telephony environment utilises RCC (remote call control).  Skype for Business server does not support RCC so those requiring this feature need to remain homed on Lync 2013.
  • Server, DNS, and certificates names reference Lync 2013 environment.  (OK, cosmetic only however I’d find this annoying!)

This article will not describe a full migration as it is only concerned with adding Skype for Business Server into a Lync 2013 environment.  The goal is to have enabled accounts on both systems able to view presence, send IMs, and share desktops.

Adding a Skype for Business Standard Edition Pool

Install prerequisites.  
Using powershell install required Windows features
Add-WindowsFeature NET-Framework-Core, RSAT-ADDS, Windows-Identity-Foundation, Web-Server, Web-Static-Content, Web-Default-Doc, Web-Http-Errors, Web-Dir-Browsing, Web-Asp-Net, Web-Net-Ext, Web-ISAPI-Ext, Web-ISAPI-Filter, Web-Http-Logging, Web-Log-Libraries, Web-Request-Monitor, Web-Http-Tracing, Web-Basic-Auth, Web-Windows-Auth, Web-Client-Auth, Web-Filtering, Web-Stat-Compression, Web-Dyn-Compression, NET-WCF-HTTP-Activation45, Web-Asp-Net45, Web-Mgmt-Tools, Web-Scripting-Tools, Web-Mgmt-Compat, Server-Media-Foundation, BITS

Create File Share
Create directory, share, and ensure correct permissions.  This lab environment will utilise a share on the local c drive of the Skype for Business server.  Microsoft recommend DFS as it provides high availability.

  1. Create directory
  2. Right click directory > properties > sharing > advanced sharing > share this folder
  3. Permissions > Add an administrator account with full control, change, read permission.

Install Administration Tool
From Skype for Business setup media run installation.

  • Installs Microsoft Visual C++ 2013.
  • Ability to have setup connect to internet to download and install updates.
  • This lab environment will install Skype for Business to default location
  • Lync 2013 is already installed Active Directory requires no further preparation
  1. Accept license terms
  2. Select Install Administrative Tools.  These tools include Topology builder.

DNS Records
As this is a simplified Std Edition deployment only a small number of DNS records were required (both records resolve to Lync 2013 standard edition server) –

  • A Record – sip.nomoredeskphone.local
  • SRV record – _sipinternaltls._tcp.nomoredeskphone.local

Topology Builder
This is where the fun begins! Defining topology.

  1. Run Topology Builder and download initial topology.  This contains the existing Lync 2013 deployment and now additional Skype for Business container.
  2. Expand Skype for Business Server > Skype for Business Server 2015
  3. Right click Standard Edition Front End Servers > New Front End Pool > Next
  4. Enter FQDN of server to add.  E.g. skype.nomoredeskphone.local.  Ensure this matches the DNS FQDN of the server otherwise server installation fails.
  5. Select components to install on front end server.  Whilst not required I am going to add enterprise voice as I intend on using it at a later stage.
  6. Select Collate Mediation Server
  7. No Edge server required for this lab.  For any production environment I recommend configuring the internal pool prior to attempting edge deployment.
  8. Accept SQL Express default installation options.
  9. Enter file share details.  Ensure directory, share, and permissions prior to this step.
  10. For this lab I have kept the base URL as is.  This would be modified in a production environment to represent the URL exposed by a reverse proxy however I do not intent to deploy external connectivity.
  11. This lab will not require Office Web Apps server therefore it is not selected
  12. A basic Skype for Business Server topology is ready to be published
  13. Select Action > Topology > Publish…
  14. Topology Builder proceeds to publish topology
  15. Take note of results when publishing complete as this screen may display errors.  Additional information may be displayed such as next steps ‘to-do list’ as per example below.
  16. Open to-do list for additional instructions

    Note – Remove Lync 2013 topology builder.  From this point onwards the topology should only be updated using Skype for Business topology builder

Skype for Business Standard Edition Installation

Local Configuration Store Installation

  1. Open Skype for Business deployment wizard
  2. Install or Update Skype for Business Server System
  3. Install local configuration store > Run
  4. Retreive directly from CMS store > Next
  5. Finish

Set or Remove Skype for Business Server Components

  1. Setup or Remove Skype for Business Components > Run
  2. On first screen select Next
  3. Finish


  1. Request, Install, or Assign Certificates > Run
  2. Select Default Certificate > Request
  3. Select CA and select sip domain(s).  Will be using standard web server certificate template for this request > Next
  4. Review Certificate details > Next
  5. When request is complete select Next
  6. Assign this certificate is selected by default > Next
  7. Certificate is assigned > Next
  8. Review summary of certificate to assign > Next
  9. Next
  10. Select next on certificiate assignment summary
  11. Finish

There is no need to assign an OAuth certificate as this was created during the initial Lync install, is still valid, and automatically replicates between servers.

Start Services
Unlike Lync 2013 the deployment wizard will not start services and this is performed using powershell.


  1. Open powershell and run the following command



  1. When prompted enter pool fqdn



Initial startup takes a few minutes.   This completes how to add Skype for Business into a Lync 2013 environment however work isn’t complete as accounts and other things such as CMS, response groups still need to be migrated.  More on those items later.

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