I have tried few days to connect to azure web role. I enabled the settings which is prompting when you going to publish the web role. But it didn't work for me. (The reason i found is i gave the name administrator ). You can following alternative way to connect to your web role. How to connect to Windows Azure Web Role (Using Remote Desktop) Create a Azure Web Role and publish it to azure. When you are publishing enable the Remote Desktop for all roles. If you use usernames such as admin, administrator, etc. it will not work. You can check it from Go to Cloud services and Configure Menu Then click the remote icon in the bottom Then it will pop up a dialog which you can use and check for your remote configurations.
MELICK RAJEE BARANASOORIYA | Enterprise Architect