A delivery scheduling system that is configured for scheduling the delivery of an item or service from a sender to an intended recipient. After receiving a signal indicating that, for example, a particular package is to be delivered to an intended recipient, the system attempts to establish interactive contact with the recipient either by direct contact with the recipient, or by leaving the recipient a message to establish direct contact with the system at a convenient time. Upon establishing contact with the recipient, the system allows the intended recipient to schedule delivery of the package. More particularly, the recipient may schedule the package to be delivered: (1) within a particular time window; (2) before or after a particular time of day; or (3) on a particular day.