A medication compliance cap system, cap assembly, and associated methodology enhance compliance of a user's prescribed or scheduled medication regimen. Central to these specifications is a “smart” or intelligent medication cap assembly that basically functions to communicate wirelessly with a remote medication compliance application or software executable via a personal computing device. A power source and signal-generating circuitry are housed within an inner cap housing and an outer cap housing, which circuitry is selectively switched on and/or off via engagement with an upper container rim of a medication container. The medication compliance application schedules medication-taking events and alerts the user when a medication-taking event is due. The user may stop the alert by removing the medication cap assembly from a medication container, at which time an alert cessation signal is transmitted to the medication compliance application.