A secure pickup and delivery container includes a lockable door, a control unit, an access element, and an anchoring element, according to one embodiment. The control unit includes a processing element and a memory that can be programmed either on-site or remotely with access privilege information such as identity (e.g. of container, delivery person, etc.), location, date, time, frequency of access, and/or package-specific information. In one embodiment, access privilege information is programmed when an intended recipient of a delivery consummates a point of sale transaction, for example over the Internet or telephone. The access element can be a keypad, a biometric scanner, a card reader, a bar-code reader, and/or a wireless control element to read a programmable token such as a smart card. Delivery personnel can enter access request information into the access element, and if it favorably compares with the access privilege information, the control unit unlocks the door. Notification can be concurrently made via wireline or wireless communications to the intended recipient, who may be situated remote from the secure container. The recipient can optionally return a delivery acknowledgment to the delivery personnel. Details of the delivery transaction can also be recorded electronically on the delivery personnel's token, within the container, or at a remote location.