So what may have worked to save money on licensing with workstations wasn’t gonna fly in a Terminal Services environment. Here’s the problem: Skype for Business Basic stand-alone cannot be installed on Terminal Server (or RDS server). Without the licensed SfB version users won’t be able to utilize VOIP calling or video conferencing, but this customer was fine with that limitation. Also notable, Office 2013 can coexist with Skype for Business 2016 Basic and the buttons for instant messaging work as expected from Outlook 2013. Not the cleanest setup, but it works for instant messaging which is all this customer desired. After realizing that SfB wasn’t part of their already purchased Office 2013 Standard volume licenses, they decided to deploy Skype for Business Basic stand-alone to all company workstations. A little background on this particular customer is that they licensed Office 2013 Standard for their users and the RDS server and then subsequently licensed SfB server and purchased SfB CALs for all users.
Install Skype for Business (SfB) 2016 Basic on an existing Remote Desktop Services Server (formerly Terminal Services) which already had a volume licensed install of Microsoft Office 2013 Standard.