The invention provides an information processing apparatus, an information processing system, and an information processing method. The purpose of the present invention is to suppress the ease of canceling a reservation and reduce the influence of canceling a reservation on a canceled side in a movement service performed by taking a vehicle that moves to a prescribed destination in a convenient manner. The information processing apparatus includes a control unit. The control unit is configured to manage reservation for a transport service for sharing a ride in a vehicle that travels to a predetermined destination; receive a cancellation request for a first reservation for the transport service provided using a first vehicle, from a user terminal of a first user who is one of a driver userof the first vehicle or a passenger user who is scheduled to get on board the first vehicle, for whom the first reservation is established; and determine a substitute driver user or a substitute passenger user for the first user, and assign a penalty to the first user, in a case where the cancellation request for the first reservation is received from the user terminal of the first user.