In a calendar messaging method and system, a calendar application executing on a computer receives a command to activate an out-of-office status, and receives one or more selected calendar events. The method and system further include automatically updating the calendar events, wherein the updating includes at least one of canceling the calendar events, and removing the user as an invitee of the calendar events. An out-of-office message is then automatically sent to at least one recipient indicating a type of update made to one or more of the calendar events.