A computer system receives user data from a computing device of a user and determines that the user will utilize a transport service to arrive at a destination location at a specified time. The computer system automatically triggers, without user input, a service request for the user by monitoring transport provider availability within a proximity of a current location of the user prior to the specified time, and determines a service request time for the user based on the transport provider availability. The computer system then generates the service request for the scheduled user event based on the service request time.