Risk-taking in the outdoors provides opportunities for young tamariki to develop their physical skills and learn to self-manage risk. Within an early childhood setting many policies and regulations are in place to ensure that tamariki are kept safe from harm. Early childhood leaders are tasked with the challenge of managing the tension between providing sufficient opportunities for tamariki to engage in risk-taking while following regulations to successfully eliminate any hazards that could cause serious harm. The scenarios and voices of the key informants presented in this article demonstrate ways that safe risk-taking opportunities can be implemented while navigating this tension.