People's lives are made easier through design and technology, whether it is a smartphone or a device that assists visually impaired people. This research explores new approaches to pillbox design for people taking medication. Pillboxes are meant to support patients with serious illnesses like HIV/AIDS for which regular medication-taking is necessary. Using electronics, experiments were conducted on different designs, forms, and structures of traditional pillboxes. This research uses a qualitative research and prototyping strategy to investigate the potential of good design on technological advancements to improve low medication adherence rates due to stigma for people living with HIV/AIDS (PLWHA) in Ghana, while also making medicine-taking a more private experience. The Pill Assist prototype is a wearable device that takes a traditional wallet design and transforms it into a dual-purpose medication storage and reminder system. This device assists people with pill-taking in a timely manner while keeping their status private. Pill Assist introduces new ways in which wearable design can be integrated into pill-taking and as a lifestyle solution. Findings from this study are an initial step toward applying good design principles and technology to develop solutions that cater to all stigma-related diseases.