An information processing apparatus determines whether or not a predetermined transfer condition for urging a target user sharing a ride in a ride-sharing vehicle with another user with a different destination to transfer between ride-sharing vehicles during movement is established, on the basis of a predicted travel route of each of a transfer source vehicle and a transfer destination vehicle. Then, in the case where the predetermined transfer condition is determined to be established, the information processing apparatus transmits transfer information for urging the target user to transfer from the transfer source vehicle to the transfer destination vehicle during movement, to a terminal associated with the transfer source vehicle and a terminal associated with the transfer destination vehicle.