Massive stars play a central role in the Galactic ecosystem. Observations and theoretical works in the past years have renewed our understanding on the origin of massive stars in the Milky Way. I will review recent progress and propose few promising directions for the future, including (1) A pan-Galaxy atlas of the filamentary ISM, (2) Dynamic mass assembly in protocluster formation, (3) The role of turbulence, magnetic fields, and monolithic massive prestellar cores for the initial conditions.