I have a terminal server setup behind a RD Gateway instance and all is working normally with one exception. Thru group policy I have "Always prompt for password on connection set". This option works perfectly well from any PC on the LAN or thru the RD Gateway. My issue happens when a user is setup on their iPad using the MS Remote Desktop Connection app. When the user creates a connection and saves the password, they are then able to connect without the prompt to enter their password. This present a security flaw as users are allowed to use their own personal devices so we cannot enforce a screen pin unless they setup email. I have looked at various settings to try and force the prompt and or prevent the pass thru from RD Gateway to the RD server but no success yet.