Mass loss bridges the gap between massive stars and supernovae (SNe) in two major ways: (i) theoretically, it is the amount of mass lost that determines the mass of the star prior to explosion and (ii) observations of the circumstellar material around SNe may teach us the type of progenitor that made the SN. Here, I present the latest models and observations of mass loss from massive stars, both for canonical massive O stars, as well as very massive stars that show Wolf–Rayet type features.This article is part of the themed issue ‘Bridging the gap: from massive stars to supernovae’.