A system and method for continuously monitoring and updating delivery schedules based on completed deliveries and customer modifications. A delivery scheduling computer stores and updates delivery schedule information, notifying the customer prior to a scheduled delivery of an estimated time of delivery. The notification is made to a customer's PC, browser-based client, hand-held computer or set-top box, or by conventional communication methods such as a telephone, pager, or cellular phone. If the customer desires to change the time or location of the delivery, the customer transmits a delivery change request and the schedule is modified accordingly. Employees use a hand-held computer or a browser-based client to receive updated delivery schedule information, as well as to transmit a delivery completion message to the delivery scheduling computer. The message includes an actual delivery time which the delivery scheduling computer uses to update the estimated delivery times of the remaining deliveries.