There is provided an information processing apparatus, an information processing method, a program, and an information processing system capable of causing a user of a destination apparatus to be aware of arrival of delivered information without the destination apparatus communicating directly with the peripheral apparatus. The information processing apparatus includes: a notification processing unit that generates notification information for causing a user of a destination apparatus to be aware of arrival of delivered information, which is directed to a peripheral apparatus that is estimated to be located within a predetermined range from the destination apparatus of the delivered information on a basis of positional relationship information; and a communication unit that transmits the notification information generated by the notification processing unit.