We adopted personal autonomy and communal participation as principles for designing services to improve older adults’ technology learning experiences. We began the research by conducting surveys and interviews to better understand how older adults use digital technologies and how their interactions with these technologies relate to their perceptions of autonomy and participation. In partnership with local senior living communities, we proposed an educational service that would improve older adults’ technology literacy through three community games that address the specific problems that older adults experience while learning digital technologies. Our research findings later influenced the design of a service to support isolated older adults during the pandemic. This project has been presented and published at the 2021 International Association of Societies of Design Research (IASDR) Conference.