Childcare settings offer an ideal opportunity for children to become acquainted with risk-taking in play, which promotes healthy growth and development. Van Rooijen and Newstead's (2016) model, based on a review of international literature, has identified the main challenges for childcare professionals when promoting risky play, namely; conflicting pressures from cultural and regulatory factors, parental concerns, personal attitudes and constructs of children. We used an online questionnaire to examine whether these challenges impact on children's risk-taking play in Dutch childcare contexts. Dutch professionals encounter barriers; especially in external regulations, organization protocols, and parental overprotectiveness. We adjusted the model to gain further insight in influencing factors and their interrelatedness in a Dutch context. Our findings indicate that professionals can be supported with knowledge about and openness in discussion on risky play and with the tools necessary to support autonomy in daily pedagogical decision-making which then supports children's age-appropriate risk-taking opportunities.