Here was the issue:
One of my child windows had a Silverlight that calling a .Net Ria Service. The service call ended in an error.
The next time several I debugged, the debugger did not attach to the child windows. I had to attach to the child windows manually.
I fixed the Ria Service call so that it did not end in an error. And had to manually attach to the child windows in that debugging session. However in subsequent debugging sessions, the debugger automatically attached.
I tried breaking the Ria Service call and I had to manually attache again. What is a little weird is that closing Visual Studio and even rebooting the machine does not make Visual Studio automatically attach again. You have to have a debugging session where the child window make a sucessful call to a Ria Service to fix it.
NOTE:
The RIA error that was breaking my debugger was caused by a misspelled include in the domain query (ie...
return Context.SOME_ENTITY.Include("Misspelled_Association_Property");
) not all RIA exceptions cause this problem.
My scenario has a number of specific cases that I will go over. I don't have all the things handy to test a more general scenario, but I will when I finish my project unless someone does this first.
Here is what I have:
I am using the a LinqToEntitiesDomainService from the July 2009 Preview release of .Net RIA Services.
To complicate things a little more, since my application is using an Oracle backend, I am using DevArt's dotConnect Entities provider as the EntityFramework model for my domain service.
When I get time, I will try this on the Nov 2009 RIA and a standard SQL backend and EF to see if I still have the same issue. If this is the case I will report it to Microsoft as a visual studio bug.