This conference is dedicated to deepening our understanding of the complex links between the lives of massive stars and their explosive deaths. Massive stars are central engines of feedback in galaxies, enriching the interstellar medium and giving rise to compact remnants that power high-energy phenomena and gravitational-wave events. Yet many fundamental questions remain unresolved: Which stars explode as which types of supernovae, and which collapse directly to black holes? How do initial conditions shape stellar evolution, mass loss, and remnant formation? And how can we connect the growing diversity of observed transients to their progenitor stars? New time-domain surveys are capturing the earliest stages of core-collapse, offering insights into the final years of stellar evolution. At the same time, gravitational-wave observatories are revealing the demographics of compact remnants. The next generation of observatories promise to expand this window even further. This conference aims to bring the massive stars and supernovae communities together in order to identify shared challenges, forge new connections, and inspire joint approaches to longstanding problems.