It seems like the problem is the type of debugging. In the project properties, make sure that you enable Silverlight debugging. On your website, right-click, go to properties, and then on the "Web" tab, the "Debuggers" section appears below. Make sure Silverlight is selected.
Sometimes a JS debugger joins the IE process, which means there is a debugger, but it just isn't the debugger you want. I think this may be the cause of this problem.
Hope this helps. Miguel
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