In many parts of the world, older adults continue to face significant barriers to digital inclusion, but the source of that inequality is not well understood. However, we do not know enough about differences among older people seeking to improve their digital skills. Examining the impact of a national three-year digital inclusion programme reaching more than 580,000 older adults in Australia, this study explores factors that affect digital skills and literacy later in life. A mixed-methods approach involving a two time-point survey (N = 337) along with participant interviews (N = 30) examined the effectiveness of programme elements. A latent class analysis was applied to examine differences in the way older adults engage with digital technologies. Qualitative analysis helped to detail those differences. Programme outcomes were far from uniform, reflecting diverse motivations, lifecourse experiences, needs and capabilities among older adults, countering much existing research that tends to elide those differences. With reference to the concept of situated literacies, we highlight the importance of life experiences, needs and motivations to the outcomes of digital inclusion interventions. Our findings emphasise the need to disaggregate older adult internet users, and account for differences in life experiences, needs and motivations in the design and delivery of digital inclusion interventions at scale.