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It is predicted that there will be more people over the age of 65 than under 5 by 2050 in developed countries. In recognition of the needs of an ageing population, there is a growing field of research in HCI focused on engaging older people with digital technologies. This thesis contributes to the field of ageing in HCI through a community-based participatory design investigation into the challenges and opportunities for older people to engage with digital tools in their everyday lives. We demonstrate how the commitments, practices and values of participatory design can be used to better understand and foster engagement between digital tools and older people through the support of community-based organisations. This is achieved through two case studies. The rst study with a traditional computer class at a local day centre. The second with a London-based intergenerational running club. The research reflects on and examines the details and decisions of the learning and adoption process across these two studies. We expand our view beyond the digital tools to the influences and situations that contribute to older people's attitudes and usage. Through the lens of participatory design and communities of practice we discuss the considerations of values, problem-solving, and identity that can potentially be transferred to other non-traditional digital learning environments for older people. We provide recommendations and reflect on our challenges to serve as guidance for other researchers engaging in similar participatory work `in-the-wild'.