The developmental benefits of taking managed risks in childhood are well documented. These include increased physical activity, improved physical, social, and mental health, and better risk-management skills. Although there is evidence supporting the benefits of managed risk in play, there seems to be a disconnect between this and the actual experiences of children in New Zealand schools. We argue that this has resulted from a growing culture of risk aversion in schools, catalysed by national health and safety reforms in 2016 that applied to all areas of industry. Context matters, and without high-level clarifications in the legislation itself, or support information from the agencies who can enable or disable play opportunities, risk aversion in the education sector is likely to continue escalating. We use the New Zealand context to argue that health and safety processes, documentation, and personnel need to acknowledge that learning to navigate risk is an important part of mitigating negative risk outcomes in all children and that this should be enabled within school environments. There are experts and tools available, such as benefit–risk assessment and dynamic risk assessment, which can support the shift away from this risk aversion. This article draws on empirical research, case studies, and personal interactions with schools over several years. We theorise that the utilisation of these more holistic health and safety processes within the education sector, and high-level clarity from the government and its agencies, will support schools to provide the necessary health and safety compliance while supporting young people to learn and develop fully.