There's an upcoming Lang.Net Symposium (Compiler Lab++) on Microsoft Campus. Kathy and Thottam have more details.
The schedule's got a lot of stuff that's sounds a lot cooler than debugging; but if you're on campus and want to chat about making your language debuggable, ping me and I'd love to talk with you.

In the past I've had people ask me things like:
- "what sort of debugging support do I get for free?"
- "my language has dynamic scoping, how do I make that debuggable"
- "I'm writing my own IDE for my language; how do I integrate a debugger"
- "how should I do codegen for language feature XYZ to make it cooperate with a debugger"