Advanced wide-field and high-cadence transient surveys have revolutionized our ability to watch supernova explosions in real time. Rapid follow-up observations and extensive numerical models have further revealed unprecedented features of dense circumstellar medium in various spatial scales as traced by the expanding supernova ejecta. Such circumstellar medium is thought to originate from mass-loss activities in the final years to decades of stellar evolution; however, their inferred densities exceed the expectations from standard theory by many orders of magnitude. In this talk, I will first introduce standard stellar evolution and supernova explosion mechanisms, and then describe novel observational probes and modeling techniques of supernovae to reconstruct their explosion properties and progenitor mass-loss histories. Finally, I will discuss our on-going largest sample study of supernovae interacting with circumstellar medium and emerging pictures of dramatic dying breaths of massive stars.