When a supernova shockwave launched deep inside the star exits the surface, it probes the circumstellar medium established by prior mass loss from the pre supernova star. The bright electromagnetic display accompanying the shock breakout is influenced by the properties of the star and scripts the history of the stellar mass loss. We investigate with MESA and STELLA codes the radiative display resulting from a set of progenitors that we evolved to core collapse. We simulate with different internal convective overshoot and compositional mixing and two sets of mass loss schema, one the standard “Dutch” scheme and another, an enhanced, episodic mass loss at a late stage. Shock breakout from the star shows double peaked bolometric light curves for the Dutch wind, as well as high velocity ejecta accelerated during shock breakout. We contrast the breakout flash from an optically thick CSM with that of the rarified medium.