Positive risk-taking in outdoor physical play is important for 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. Perceptions of risk are very much subject to cultural interpretation, and the growing risk aversion evident in some developed Western countries, namely Australia, the United Kingdom and the United States, is less obvious 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 asked about the outdoor play experiences they provide for children and their attitude towards risk-taking in play. Results showed that 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 play space, regulations, and threat of litigation were identified as constraints for the Australian practitioners. These findings have implications for the development of policy supporting teachers’ pedagogical decision to provide developmentally challenging play environments for children.