A system and method for generating and sending reward messages to users accomplishing goals related to a personalized health behavior plan. Rewards may be issued for reasons such as achieving an ultimate goal, reaching an intermediate goal, or completing a suggested activity such as eating a suggested meal or performing a suggested physical activity. A reward may be a coupon for use at an establishment such as a restaurant, a clothing store, or a fitness center. Rewards may also be checks sent through postal mail or coupons for printing on a personal printer. Reward messages are generated by an expert system based on a user's personalized diet, exercise, or other health plan, goals associated with the plan, and specified preferences. Reward messages are sent to user's portable devices. Current location information may be used to send a user a reward for use at a nearby establishment.