A delivery system applies rules for authorizing transactions to a recipient that are individualized for each recipient. These rules may limit the number of items available for the purchaser to purchase for a recipient, the types of items available for purchase for a recipient, and the price of the items for the recipient. The system automates the delivery of the item to the recipient via a kiosk, such as a vending machine. An identification device of the vending machine identifies the recipient. The vending machine dispenses the items to the identified recipient.