Methods and systems for enabling and supporting patient compliance with a health treatment program or with health-related instructions from a caregiver are described. An interactive feedback loop is implemented that enhances and improves on present methods of monitoring and supporting patient compliance with treatment programs, particularly for patients with chronic conditions. A patient enters various types of data (e.g., biometric readings, diary entries, responses to surveys and health assessments, etc.) to a health data management system that includes a patient compliance monitoring system. The patient is encouraged to enter as much data as is practical and as frequently as possible. The feedback loop of the present invention provides compliance messages to the patient in a timely manner that are responsive to the data entered by the patient. The messages are customized, supportive, and timely. The system can also implement a reward scheme in which patients who go beyond their prescribed treatment program or consistently stay within a compliance range obtain direct financial benefits or rewards. The system also allows patients to sends feedback on the messages he or she receives from the system. This feedback can be used to measure the effectiveness of a treatment program or of the monitoring system itself. Healthcare professionals play an active role in tailoring and "signing off" the compliance-related messages that the patient receives.