This cross-cultural multiple case study investigates the approaches of educators in nature-based preschools in Turkey and Germany towards risky play, exploring factors influencing play behaviours and educator roles. Four educators from Turkey and three educators from Germany participated in the study. Through qualitative analysis of interviews and observations, three themes emerged: factors affecting play (including age, gender, environment, and cultural norms), educator roles (pre-play, during play, post-play), and risky play requirements (rules, risk management). Findings reveal cultural differences in attitudes towards risk, the impact of policy frameworks on practice, and the importance of professional development for educators. Policy implications include the need for supportive regulations promoting outdoor play, while future research should focus on longitudinal studies to assess long-term outcomes of risky play and explore innovative approaches to risk management. This study underscores the importance of creating environments that empower children to engage in enriching, developmentally appropriate play experiences while ensuring their safety and well-being.