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I have a two server setup, one running Gateway and Web, the other running Session Host. I have a RemoteApp onfigured to run from the session host. I've set it up with an external CA generated certificate on the Gateway and an internal cert on the session host.

I have created a .rdp file for the RemoteApp, and when I distribute that to users they are able to launch the RemoteApp successfully. However, when they log in to the RDWeb portal and attempt to launch the RemoteApp from there, they receive the following error:

Your computer can't connect to the remote computer because the Remote Desktop Gateway server is temporarily unavailable. Try reconnecting later or contact your network administrator for assistance.

Things I have tried:

  • Configured the RemoteApp properties on the session host to use the Gateway (specified by it's FQDN, same as in the .rdp file which works)
  • Configured the DefaultTSGateway property in IIS Application settings on the Web/Gateway server
  • Verified that all application pools are configured with Enable 32-bit Applications to FALSE I have tried multiple authentication methods on both servers. Everything works when using the .rdp file, but I can't get it to work wit the RDWeb portal.

Any suggestions?

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