Ok, I have a Server 2008 Terminal Server and I have all the TS roles installed on the same server. I am able to connect to the TS Web page through TS Gateway but it is asking for a password when you initially go to the site before it shows the published apps. After that password is entered and the published apps appear, I click on an app and it takes a bit and eventually I get the Connecting to App window with the "Details" button automatically selected to show the server 2008 login screen through RDP. My question is why am I getting this second password prompt? Shouldn't my initial authentication to TS Gateway be used for TS Web? Under the RemoteApp settings I have selected "use the same credentials for TS Gateway for terminal services" and I thought that should take care of it.