A computer system can receive user data from a computing device of a user, and based on the user data, determine that the user will utilize a transport service to arrive at a destination location at a specified time. The system can monitor transport provider availability within a proximity of a current location of the user prior to the specified time. The system can then determine a service request time for the user based at least in part on the transport provider availability, and automatically generate the service request for the user at the service request time to match the user to a transport provider.