Injury prevention plays a key role in keeping children safe, but emerging research suggests that imposing too many restrictions on children’s outdoor risky play hinders their development. We explore the relationship between child development, play, and conceptions of risk taking with the aim of informing child injury prevention. Generational trends indicate children’s diminishing engagement in outdoor play is influenced by parental and societal concerns. We outline the importance of play as a necessary ingredient for healthy child development and review the evidence for arguments supporting the need for outdoor risky play, including: (1) children have a natural propensity towards risky play; and, (2) keeping children safe involves letting them take and manage risks. Literature from many disciplines supports the notion that safety efforts should be balanced with opportunities for child development through outdoor risky play. New avenues for investigation and action are emerging seeking optimal strategies for keeping children “as safe as necessary,” not “as safe as possible.” This paradigm shift represents a potential for epistemological growth as well as cross-disciplinary collaboration to foster optimal child development while preserving children’s safety.