An out of office auto-response system that generates a calendaring user interface through which multiple out of office periods can be managed. The calendaring user interface enables a user to define, simultaneously view, and/or modify, multiple out of office periods during which auto-response messages will be generated. The out of office periods of the disclosed system are manageable as a specific type of calendar entries, and/or as a settable attribute of various types of calendar entries (e.g. vacation type calendar entries, meeting type calendar entries, etc.). The system generates user interface objects that allow a user to define an out of office period as repeated. The repeated office action may be defined as repeated a user-specified number of times, and over a user-specified interval, e.g. daily, weekly, monthly, yearly, etc.