Early Childhood services are becoming an increasingly significant part of children’s lives. As such they offer vital opportunities for children to engage in physically challenging active play in a safe and secure environment. However, in an increasingly ‘risk averse’ society an over-emphasis on safety has seen such play opportunities eroded. This qualitative study explored Early Childhood practitioners’ (n = 17) beliefs about risk-taking and their provision of ‘risky’ play opportunities in the outdoor environment. The findings suggest that from a pedagogical perspective, practitioners believe opportunities for risk-taking are important for all aspects of children’s development however the regulatory environment places constraints on their ability to provide sufficiently challenging experiences. The research findings support the call for more flexible enforcement of regulations to allow practitioners to use their professional knowledge to make informed decisions in risk situations.