The ageing of Western societies is often viewed as a challenge or even a problem. In this context, digital “solutions” are increasingly promoted as essential components of strategies to address related issues. Nevertheless, projects to develop and implement technology in healthcare and social care frequently fail. One reason for limited adoption or poor fit of these technologies is an insufficient understanding of the social realities and live worlds of older (potential) end users. Participatory approaches to developing technology address this and offer considerable scope. However, they are beset with challenges, such as the “participation dilemma” and the risk of (un-)consciously remaining at a tokenistic level of involvement. Furthermore, issues such as ageism are often relegated to reflexive approaches, where recommendations typically emphasize the need for reflection but lack concrete guidance on the process and systematic strategies to address ageism at structural and individual levels. This contribution addresses that gap by offering a sociohistorical contextualization of ageism and investigating the advantages and challenges associated with participatory approaches in this setting. Additionally, it presents approaches to systematically make ageism transparent and effectively counteract it at structural and individual levels.