Provided is an information processing system, an information processing apparatus, and an information processing method, which are capable of achieving all of crime prevention, disaster prevention, and activation of local community by appropriately conveying an indoor state to the outside while distancing from physical contact. The information processing system includes a detecting unit that detects a feeling of one or more persons located indoors on the basis of sensor data obtained by sensing an indoor state; and a control unit configured to perform control such that a captured image obtained by imaging the indoor state is output to an outdoor display apparatus in a case in which a value of a feeling of at least any one person among the detected feelings satisfies a predetermined condition.