This application relates to automatically scheduling timeslots, such as timeslots for scheduling item pickups and deliveries. The embodiments may employ machine learning process to determine, for each of a plurality of timeslots, a timeslot capacity. The embodiments may further determine a time as to when each of the plurality of timeslots become available for selection, such as on a webpage. In some examples, the time determined to make available for selection each of the plurality of timeslots is based on a predetermined amount of time before the timeslot. Further, the embodiments may provide for display each of the plurality of timeslots at the determined time. The embodiments may further include receiving a selection of one of the plurality of timeslots, and scheduling a pickup or delivery based on the selected timeslot. The machine learning processes may be trained with features generated from historical timeslot data and workforce availability.