I'm not sure what the pattern of behaviour is but some programs - notably simple rack.ru based ones running in thin - can't easily be debugged. When a breakpoint is tripped, no source is available
Note this isn't the same as this other S.O. [issue][1]
[1]: http://stackoverflow.com/questions/323010/in-ruby-why-does-my-irb-interactive-debugging- session-always-say-no-sourcefile