Install Skype for Business Server 2019

What is Skype for Business Server?

Skype for Business Server provides instant messaging, presence, conferencing, video, and telephony services. This step by step guide will walk you though to install and configure Skype for Business Server 2019 in virtual lab.

Lab instructions

Domain – techbooster.cloud
All the virtual machines have been hosted on VMware workstation
Servers have been installed with Windows Server 2019 Standard evaluation edition, client machines have been installed with Windows 10 Enterprise evaluation edition and Skype for Business 2019 evaluation edition has been used (Check out the download links below)
Since this is a lab ‘Default administrator’ account has been used in all occasions but this is not a recommended best practice in real world environment due to security reasons
Standard user accounts ‘tbuser1‘ & ‘tbuser2‘ have been created
Internet access enabled on all the hosts for lab easiness, again you wouldn’t do this in real world for security reasons
DC1 provides domain and DNS services
Static IP addresses have been assigned to all the hosts and no DHCP services involved
Client machines (DP1 & DP2) have been installed with Skype for Business Basic version
Prerequisites (Latest version of .NET Framework, Silverlight & UcmaRuntimeSetup) files have been copied to VM’s

Virtual Machines and details

Skype for Business Server 2019 - VM Description — Skype for Business Server 2019 – VM Description

Stage 1 – Prepare the environment

Step 1 – VM Setup Create the virtual machines (VM), update the hostnames and assign IP addresses accordingly (you can use the above table if it’s easy for you) Step 2 – Enable Domain & DNS services on DC1 and join other hosts to the domain Step 3 – Create standard user accounts (tbuser1 & tbuser2) Step 4 – Create DNS records for Skype service on DC1

From Server Manager > Tools > DNS > DC1 > Forward Lookup Zones > Right-click on the domain (techbooster.cloud) > Other New Records > Select a resource record type > Service Location (SRV) > Create Record. Enter the following records,

Service: _sipinternaltls, Protocol: _tcp, Port number : 5061, Host offering : DC3.techbooster.cloud and click OK
Service: _sip, Protocol: _tls, Port number : 443, Host offering : DC3.techbooster.cloud and click OK and Done

Skype for Business Server 2019 - sipinternaltls — Skype for Business Server 2019 – sipinternaltls

Skype for Business Server 2019 - sip entry — Skype for Business Server 2019 – sipinternaltls

Step 5 – Install Certificate Services on DC2

From Server Manager > Manage > Add Roles and Features > choose the default configurations > Select ‘Active Directory Certificate Services‘ > Add Features > 3x Next > Install
When you see the Configuration required notification on the wizard click ‘Configure Active Directory Certificate Services on the destination server‘ > Next > Select ‘Certification Authority‘ > 4x Next > In the ‘Specify the name of the CA‘ stage, change “techbooster-DC2-CA” to “ROOT-CA” > 3x Next > Configure > Close and Reboot DC2

Step 6 – Switch to DC3 to prepare before install Skype for Business Server 2019

Create a shared folder. Click ‘File Explorer’ > C:/ > Create a folder named “Share” > Enable share > Add local and domain Administrator accounts and grant full permission
Mount the Windows Server 2019 ISO file to any drive (Assume it’s mounted to D drive). And the from Server Manager > Manage > Add Roles and Features > In the Features selection – Select ‘.NET Framework 3.5 Features’ > Next > at the ‘Confirmation’ stage, click ‘Specify an alternate source path’ > Enter path as ‘D:\sources\sxs‘ (If ISO file is mounted to D drive) > OK > Install > Close the wizard
Install Slilverlight & UcmaRuntimeSetup applications and reboot DC3
Start > Windows PowerShell > enter the below to enable few windows features > Hit enter

‘Add-WindowsFeature RSAT-ADDS, Web-Server, Web-Static-Content, Web-Default-Doc, Web-Http-Errors, 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, Telnet-Client‘

Once the installation is successful reboot DC3

Stage 2 – Install & configure Skype Server

Step 7 – Install Skype for Business Server 2019

Run ‘Setup.exe‘ from OCS_Eval\Setup\amd64 folder with elevated administrator privileges > If you have the latest setup file then skip the update check > Install > Accept License agreement > OK
Once you are in the ‘Deployment Wizard’

Click ‘Prepare Active Directory‘ > and then
- Prepare Schema > Run > Next > Finish
- You can skip this step if you’re following all the steps accordingly if not click ‘Help’ and make sure all the configurations are updated
- Prepare Current Forest > Run > Next > Change the Location to ‘Domain FQDN‘ and enter your domain name (techbooster.cloud) > Finish
- Verify Replication of Global Catalog > Click ‘Help‘ and make sure all the configurations are replicated
- Prepare Current Domain > Run > Next > Finish
- Verify Replication in the Domain > click ‘Help‘ and make sure all the configurations are replicated on DC1 (E.g. Relevant AD Groups are created) and update the below
- Switch to DC1 > Server Manager > Tool > Active Directory Users and Computers > Users > Find ‘CSAdministrator‘ security group > Add domain administrator account as a member of the AD group
- In the ‘Deployment Wizard‘ > Click ‘Back‘
Click ‘Prepare first Standard Edition server‘ > Next > Finish
Click ‘Install Administrative Tools‘ > Next > Finish
Start > Skype for Business Server Topology Builder > In ‘Topology Builder‘ select ‘New Topology‘ > Enter a file name and save in a location
Enter the FQDN (techbooster.cloud) as ‘Primary SIP domain‘ > Skip the additional supported domains > Define the first site name (Techbooster) > Enter the site details > Next > Finish
In ‘Define the New Front End pool‘ stage click next > Enter FQDN as ‘DC3.techbooster.cloud‘ and select ‘Standard Edition Server‘ > Next > Enable the following features ‘Select Conferencing‘, ‘Enterprise Voice‘ and ‘Call Admission Control‘ > 6x next with default configurations > In ‘Select an Office Web Apps Server‘ stage click new > Enter ‘Office Web Apps Server FQDN‘ > OK > Finish
Right click on ‘Skype For Business Server‘ > Edit Properties > Scroll down and add ‘Administrative access URL‘ (E.g https://skype.techbooster.cloud) and from the drop down list select ‘Central Management Server (DC3.techbooster.cloud) > click OK
Right click on ‘Skype For Business Server‘ > Publish Topology > 2x Next > Finish

Run the Skype setup again > Once you are in the ‘Deployment Wizard‘ > Click ‘Install or Update Skype for Business Server System‘

Install Local Configuration Store > Run > In ‘Configure Local Replica Central Management Store‘ make sure ‘Retrieve directly from the Central Management store‘ is selected >
Next > Finish
Setup or Remove Skype for Business Server Components > Run
Request, Install or Assign Certificate > Run > On the certificate wizard, click Request > Update the standard details > Select the SIP domain > 3x Next > Finish > 2x Next > Finish
Click Assign > 3x Next > Finish > Close
Start > Windows PowerShell > Type Start-CsPool > Hit enter > PoolFqdn = DC3.techbooster.cloud > Hit enter > Type A and hit enter (This will start all the relevant Skype services) > Once all the services are started close the PowerShell window
You can check the optional tasks and close ‘Deployment Wizard‘

Step 8 – Enable Skype access for the created users in Step 3

Start > Skype for Business Server Control Panel > Supply Administrator Credentials > Users > Enable users > Click add and add the users one by one(tbuser1 & tbuser2) > OK > In ‘Assign users to a pool‘ select the pool from drop down list (which we have created in Step 7 DC3.techbooster.cloud) > Make sure to select ‘Use the user principal name (UPN)‘ as ‘Generate user’s SIP URI‘ > Click Enable
Click Topology > Make sure Skype Server status is Green (If not try to start the services manually/ reboot the server would help)

Skype for Business Server 2019 Control Panel

Stage 3 – Testing phase

Step 9 – Test our setup

Login to DP1 & DP2 with relevant user accounts (tbuser1 & tbuser2)
Start > Skype for Business 2016 > First things first, enable updates/ skip for now
Skype for Business will be auto-signed in with the relevant accounts
If you encounter any issues, makes sure client machines can reach DC1 & DC3 and check the UPN (It should be [email protected] & [email protected])