A practical system to remind and assess medication adherence of patients with HIV/AIDS will be designed. The long-term goal is to expand the system to motivate adherence across multiple chronic conditions. Phase I of this project will involve running a feasibility study to determine whether the system can engage a user and affect adherence over a three month period. The prototype will be designed based on usability testing of a cell phone for receiving and sending reminder messages. Adherence assessments will be performed through self-reports from the phone. These self-reports will be validated with a composite adherence measure through the study. The overall system will be initially tested using data from patient use-case scenarios. Innovations in dynamic and personalized content will be implemented through this study. Phase II of this project will entail the development of an interactive component for patients and providers. A link will be created with the study hospital’s electronic medical record to integrate medication details directly from the pharmacy. The software system will be refined through usability studies. A powered clinical study will be performed to evaluate the system’s ability to improve the adherence to HIV/AIDS medications over time. It is expected that this system will engage patients more with their care and become a robust model for patient-centric disease management.