Sensor networks are increasingly commonplace in visions of smart cities and future healthcare systems, promising greater efficiency and increased wellbeing. However, the design of these technologies remains focused on specific users and fragmented by context, overlooking the diversity of needs, wants and values present when technologies, people, and lived realities interact within instrumented spaces. In this paper we present a workshop method – Sensing Care – that can help researchers, interdisciplinary design and development teams, and potentially affected users, to explore what it takes to design for living with sensor technologies that intersect and interact across private and public spaces, through speculative scenarios and role play. Drawing from three deployments of the workshop, we discuss how this approach supports the design of future care-oriented sensor networks, and helps designers understand what it means to live with complex technologies as people traverse diverse contexts.