@oBFusCATed
I'd like to see screenshot so that I can see what you think the correct appearance of the system should be after the boost assert fails. For me it does seem to break in the debugger, but I don't know how you or the OP think this break should correctly be displayed. My understanding of WX/scintilla is that the appearance should be more or less platform independent, so a screenshot from a working CB implementation should resolve this. And it will take you, what? - two minutes to do?
To be explicit, I'd like to see the debugger call stack window and the editor window.