An automated shopping system and method in which a user places an order for at least one provider, a degree of matching between each order-provider pairing is computed as a score by an iterative scoring system, scoring correction takes place when the score is determined to be incomplete, and the score, and optionally a ranking of providers is reported to the user. The iterative scoring system includes a scoring correction system that determines whether a score is based on complete information or whether additional information and determination of a revised score is required. Additional information from outside the system may be requested including requesting information determined to be incomplete from the user or the provider and/or requesting verification of provider information from a third party, and the score may be updated to obtain a revised score based on the additional information received.