A problem we ran into with Winsitter was that we were not able to make changes within our web role and instantly see them when we refreshed. Instead, we would have to stop debugging and re-deploy the application to the development emulator.
This can get particularly annoying when you do it for the 395th time, so I tried to figure out how to fix it.
Inside your Cloud project file (the one with roles and service configurations), you'll want to unload it (right-click, Unload Project).
Next, right-click on the unloaded project and selected Edit. This will open a text version of your project within Visual Studio.
Look for a line that looks like this:
Delete it, or comment it out (that's what I did).
Restart the debugger and you should now be able to edit and continue within your Azure web applications.