This article discusses sociotechnical challenges of technology-based interventions to address loneliness in later life. We bring together participatory and multidisciplinary research conducted in Canada and Australia to explore the limits of digital technologies to help tackle loneliness among frail older people (aged 65+). Drawing on three case studies, we focus on instances when technology-based interventions, such as communication apps, were limiting or failed, seeming to enhance rather than lessen loneliness. We also unpack instances where the technologies being considered did not match participants’ social needs and expectations, preventing adoption, use, and the intended outcomes. To better grasp the negative unintended consequences of these technological interventions, we combine a relational sociological approach to loneliness with the Strong Structuration Theory developed by sociologist Rob Stones. This combined lens highlights the connection between sociotechnical factors and their agentic and structural contexts, facilitating a rich understanding of why and when technologies fail and limit.