A growing body of research has provided evidence of both children’s desire for challenging play that involves a degree of risk-taking and the role that positive risk-taking has in fostering children’s optimal health and development. At the same time, there is mounting concern that Western societies are becoming increasingly risk averse with many everyday activities now being seen as dangerous and something to be avoided. Consequently, safety concerns and stringent risk minimisation strategies are eroding children’s opportunities to take sufficient risks in play in order for their playground experiences to be interesting and developmentally challenging. This paper presents the argument that factors such as the Early Childhood (EC) regulatory environment, high child-staff ratios, poor outdoor environments, fear of litigation and an inadequate understanding of the benefits of risk-taking contribute to minimisation of opportunities for risk-taking play. Possible outcomes resulting from these measures include changes to both the quality and quantity of physical play, poor evaluation of risk situations, and increases in unsafe risk-taking. The present study examined these factors through semi-structured interviews with 17 Early Childhood practitioners (16 female, 1 male) recruited from 6 EC centres located in different regions of Sydney. 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 interesting and developmentally challenging experiences. The research findings support the call for more flexible enforcement of regulations and risk assessment procedures to allow practitioners to use their professional knowledge to make informed decisions in managing risk situations.