It is estimated that 200 children per day worldwide develop Juvenile Diabetes (JD). There is no cure for JD, therefore treatment protocols focus on controlling the disease. Several information systems (IS) have been developed to help patients manage their chronic diseases, but often these systems suffer from reduced use over time or complete abandonment. Limited research has been conducted that examines continued usage in this domain. Through this study, our purpose is to build and evaluate a mobile/web based JD monitoring system combined with a rewards program designed to increase continued system use. We propose a comprehensive continuance intention model by combining the IS Continuance Model proposed by Bhattacherjee with DeLone and McLean’s IS Success Model. We also explore the role of the context specific constructs of Interaction Quality and Perceived Disease Management Effort and the moderating role of several individual factors on relations in the proposed model. We propose a longitudinal study utilizing a survey methodology to empirically validate the proposed model. Data analysis will utilize structural equation modeling using partial least squares. Participants in this survey consist of adolescent JD patients and their parents, allowing us to understand the factors which are most relevant to each stakeholder group.