Learning how to respond appropriately in risk situations comes not only from the child’s direct experiences but also through the guidance of those around them. The role of parent practices in guiding children’s decision-making in risky situations has mainly been investigated in experimental contexts. The present study examined children’s risk-taking behaviour and parent responses in everyday outdoor play settings. Parents’ own risk-taking beliefs and behaviours were assessed using the Attitudes Towards Risk Questionnaire (ATR). Interviews explored parents’ attitudes towards children’s risk-taking and parents (11 mothers, one father) were observed as they supervised their four- to five-year-old children on playground equipment at a park. Parents’ ATR scores were predictive of children’s risk-taking behaviour. Parents mainly supervised their child’s play and provided encouragement and support to foster children’s engagement in challenging use of the equipment. Parents rarely intervened to prevent children’s risky play but provided advice on how to complete the activity safely. Parents emphasized that their responses to children’s risk-taking are context dependent.