Cardiovascular diseases in patients living with HIV is increasingly taking its toll on communities in rural parts of Western Kenya. Telemedicine offers an avenue for addressing the management of Non Communicable Diseases (NCDs) in these regions. In this paper, we describe the design of the Medication Management Companion (MMC), an integrated desktop and mobile application designed to better support the efficacy, safety, and personalization in the prescribing of medication and management of hypertensive patients living with HIV. By adopting principles of community practices around HIV and hypertension management, we seek to understand how medication technologies should be designed and used. Our design explores how practices such as understanding the economic challenges of patients and building trust between patients and medical practitioners within a community can bring new opportunities in the design of sustainable technology that supports management of these conditions.