Broadly speaking, adults aged 65 and older are not as technologically literate as younger populations. They do not seek digital services, such as online banking and ridesharing services, as readily as younger people and are therefore isolated from these services’ benefits. In this project, 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 are interrelated with their sense of autonomy and participation. Factor and cluster analyses were used to determine the correlation between older adults’ self-autonomous behaviours and the digital technologies they use daily. Employing quantitative and qualitative analyses, we developed three types of personas based on older adults’ technology-literacy levels, motivations, and barriers. In partnership with a local senior living community, we proposed an educational service to improve older adults’ technology literacy and prototyped three community games to address the specific problems that older adults experience while learning digital technologies. Due to the outbreak of theCOVID-19 pandemic, we remotely tested these games with coordinators and educators from local senior centres. This research’s findings also influenced the design of a service to support isolated older adults during the COVID-19 pandemic.