A method and meeting scheduler are provided for automated meeting insertion and rescheduling for busy calendars. An electronic calendar meeting scheduling program stores meeting automation properties defined for each scheduled meeting. The electronic calendar meeting scheduling program stores meeting attendee automation properties defined for each attendee of each scheduled meeting. The electronic calendar meeting scheduling program utilizes the stored meeting automation properties and the stored meeting attendee automation properties to calculate a conflict score and action list for each potential time block for automated meeting insertion and rescheduling. The calculated conflict score and action list for each potential time block for rescheduling a meeting are based upon multiple factors including a move score, a leave early score, and a shorten meeting score. The action list includes an entry for each meeting altered for automated meeting insertion and rescheduling.