This chapter brings attention to the mechanisms of ageism in the design and implementation of socio-technical interventions targeted at older adults. Drawing on findings from Digital Storytelling workshops with six 80+-year-olds at care homes in Japan and Canada, the chapter identifies contexts and conditions that undermine the agentic involvement of older participants in intervention studies. While the Digital Storytelling workshops generated positive outcomes and created opportunities for participants to redefine themselves and influence others, there were power imbalances in the story production phase. Engaging with an actor-network approach, the interplays of technologies, built environments and institutionalised concepts of old age are examined. Findings show that the empowering potentials of Digital Storytelling were contingent on participants negotiating and confronting forms of age discrimination that reverberate through technologies, care services, facilitators' expectations, and participants' own self-perceptions. Where many socio-technical interventions have failed to meaningfully involve older adults and have upheld stereotyped views of older adults' technological needs, this chapter forges connections between key factors that influence older adults' positioning within socio-technical interventions.