The present technology relates to an information processing apparatus and an information processing method enabling a vehicle to readily pass an oncoming vehicle in a narrow road or the like. The information processing apparatus includes a map generating section generating map data associated with a circumference of a vehicle, and updating the map data in conformity with a movement of the vehicle, and a waiting space detecting section detecting a waiting space enabling the vehicle to wait on the basis of the map data, and generating waiting space information as information associated with the detected waiting space and used in setting of an escaping route on which the vehicle is escaped in order to pass an oncoming vehicle. The present technology, for example, can be applied to a vehicle controlling system which performs control of automatic driving.