I have a Windows 2012 server which we are testing with RD Gateway and 2 Windows 8 workstations. To test the RD Gateway I change the entry in the Host file to redirect my TSGateway from the production system to the Test system. Now the strange part is that I can open and view the RD Gateway default web page from a Windows 8 system that was upgraded from Windows 7, but a Fresh install of Windows 8 fails to view the default web page. The fresh load can ping the TSGateway by name and replies with the correct address, so I know that part works. If I change to my production Windows 2008 TS Gateway server, both the upgraded and fresh install system connect without a problem.
Is there something new in Windows 8/IE 10 that causes problems when trying to use the Host file for HTTPS sites?