Positive risk-taking in the context of outdoor physical play is important for fostering children's optimal health and development. Despite this, there is mounting concern that many developmentally beneficial activities are now seen as dangerous and something to be avoided. However, perceptions of risk are very much subject to cultural interpretation, and the growing risk aversion evident in some developed Western societies, such as Australia, the United Kingdom and the United States of America, is less apparent in other developed countries, notably some of the European and Scandinavian countries. To explore some of these cultural differences, early childhood practitioners from Australia and Norway were interviewed regarding their provision of outdoor play experiences for children and their attitudes towards risk-taking in play. Practitioners from both countries recognised the importance of risky play for children's development and well-being. However, differences in the extent to which children's risky play was supported were evident. Factors associated with the quality of the outdoor environment, regulatory requirements, and a litigious environment were identified as constraining teaching practice for the Australian practitioners. The findings have implications for the development of policy that supports teachers' pedagogical decisionmaking in providing developmentally challenging play environments for children.