This paper presents DI@L-log, a telemedicine prototype solution under development in Northern Ireland which is being designed to extend meaningful contact with the hospital and improve care for a mature cohort of Type 2 hypertensive patients. The recent surge in telecommunications technology can help prompt patients to adhere to self-care regimens using asynchronous, automated communication via their telephone. The system proposed aims to extend care to accommodate the shifting paradigm of care into the home environment, provide feedback and timely intervention to the patient, and decision support for health professionals. The Internet and Spoken Dialogue Technology (SDT) provides healthcare with a tool for effective telemedicine delivery. We argue the potential basis for our system is to provide pro-active motivation and incentive over the stagnant paper logbook currently used to document home-monitored patient data.