I have a Server 2008 R2 Remote Desktop RemoteApp server configured to run Blackbaud for a particular group. When I launch the app (either from a .RDP file or from the Web Access portal) the app never launches. When I check the RDP sessions on the server, the session I launched for the app stays active for a few seconds, then goes to disconnected. If I run the app a second time it then launches two sessions of the app. I can also get the Blackbaud app to launch if I run another another RemoteApp app from the server, such as Calc or Powershell. It works both if I launch Blackbaud first and then the second app, or if I launch the second app first and then launch Blackbaud. Either way, Blackbaud will not launch without a second connection running. The other apps all launch without issue and seem to work normally - Blackbaud is the only app that has the problem.
The app worked fine during testing (on a different network, so we're thinking it may potentially be a firewall issue) and the app is configured for SSO with a digital certificate from our local CA. Any help is appreciated.