Locating and fixing bugs is a well-known time consuming task. Advanced approaches such as object-centric or back-in-time debuggers have been proposed in the literature, still in many scenarios developers are left alone with primitive tools such as manual breakpoints and execution stepping. In this position paper we explore several advanced on-line debugging techniques such as advanced breakpoints and on-line execution comparison, that could help developers solve complex debugging scenarios. We analyse the challenges and underlying mechanisms required by these techniques. We present some early but promising prototypes we built on the Pharo programming language. We finally identify future research paths by analysing existing research and connecting it to the techniques we presented before.