Designing systems to support the social context of personal data is a topic of importance in CSCW, particularly in the area of health and wellness. The relational complexities and psychological consequences of living with health data, however, are still emerging. Drawing on a 12+ month ethnography and corroborating survey data, we detail the experiences of parents using Nightscout-an open source, DIY system for remotely monitoring blood glucose datawith their children who have type one diabetes. Managing diabetes with Nightscout is a deeply relational and (at times) contested activity for parent-caregivers, whose practices reveal the tensions and vulnerabilities of caregiving work enacted through data. As engagement with personal data becomes an increasingly powerful way people experience life, our findings call for alternative data narratives that reflect a multiplicity of emotional concerns and social arrangements. We propose the analytic lens of caring-through-data as a way forward.