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Although telemedicine has expanded rapidly in recent years, its implementation remains uneven and is strongly influenced by regulatory, organisational and socio-technical contexts. While regulatory and legal frameworks are increasingly recognised as obstacles to the adoption of telemedicine, there has been limited empirical research examining how these frameworks interact with everyday healthcare practices. This article addresses this gap by analysing telemedicine as a regulated technological innovation from a socio-legal perspective. We examine how national telemedicine policies are translated, reinterpreted or resisted within local healthcare organisations, focusing on recent regulatory reforms in Italy. Drawing on three qualitative, multi-method case studies of telemedicine services — geriatric and cardiological telemonitoring, and territorially based nursing and GP-led services — the study explores the translation, reinterpretation, and resistance of telemedicine policies within local healthcare organisations. Data were collected through document analysis, focused observations, and in-depth interviews with healthcare professionals, managers, engineers, administrators, and caregivers. The findings demonstrate that regulatory ambivalence, arising from overregulation, underregulation and legal pluralism, produces contradictory effects. While regulatory uncertainty can foster bottom-up innovation and professional role reconfiguration, particularly among nurses, it can also generate organisational paralysis, professional misalignment and defensive practices, particularly among general practitioners. Furthermore, misalignments between telemedicine regulation, privacy law, and digital infrastructures, such as electronic health records, result in persistent 'regulatory disconnections' in daily practice. We argue that Italian telemedicine regulations are emblematic of the inefficient implementation of many health policies due to ongoing processes of legal and socio-technical translation, which produce locally situated 'nomospheres' that coexist with, and sometimes diverge from, formal regulations.