I am having issues relating to my RD Gateway server when attempting to connect from outside of my local network.
My RD environment consists of a single server (RDSH, RD Gateway, etc.), Windows 8/8.1 clients, and Mac/iOS clients using Microsoft's Remote Desktop app.
I previously had issues connecting via the RDWeb Access and RemoteApp and Desktop Connections, but those problems seem to be resolved (no changes were made to fix the problems and I will have to perform further testing to be sure these issues no longer exist).
Using Microsoft's new Remote Desktop app (via iOS or OS X), it will populate the remote resources but when I try to connect to a program, I get the error "The gateway failed to connect with the message: 404 Not Found"
The only thing I can imagine that would be causing these issues would be the RD Gateway or possibly an IIS setting. Again, all three of these methods work just fine internally (which I assume is because it is ignoring the RD Gateway).