A system and method for remotely monitoring a patient and for training the patient to comply with a treatment plan for a health condition. A patient computing device collects data relating to the patient's health condition and transmits the data to a clinician computer via a communication network. The data is analyzed in the clinician computer to determine an educational need of the patient for treating the health condition. An educational program corresponding to the patient's educational need is selected and a pointer to the educational program is embedded in an electronic message to the patient. The educational program is started on the patient computing device by selecting the embedded pointer in the electronic message. As the patient works with the educational program, new data relating to the patient's health condition is collected in the patient computing device and transmitted to the clinician computer for analysis. With this continuous feedback loop between the patient and clinician, the clinician is able to monitor the patient's progress and effectively train the patient to comply with the treatment plan.