Hypertension is the most common chronic disease affecting older adults (65+) in the United States. Unfortunately, many struggle to adhere to their antihypertensive medications as only about half diagnosed with the disease have it controlled. Therefore, there is a need for designing supportive medication management systems to aid this population with their antihypertensive medications, especially using increasingly adopted technologies such as smartphones. The preferences of older adults with hypertension must be considered when designing such systems for this population. Six older adults participated in structured interviews to inform the design of the Medication Education, Decision Support, Reminding and Monitoring System (MEDSReM). Results revealed management needs, design insights, and reminder preferences, as well as mostly positive opinions regarding technology use for medication management. These findings informed the development of MEDSReM with the goal of supporting older adults in successfully managing their antihypertensive medications.