This study aims to examine (a) whether preschool teachers’ risky play attitudes differ in relation to school type, number of children, presence of teachers’ aides, professional experience, age groups, and daily outdoor times, and (b) preschool teachers’ self-reported practices about risky play outdoors. The existing literature on risky play focuses on the crucial role of preschool teachers in children’s risk play opportunities (Sandseter et al., 2021; Van Rooijen et al., 2020). Ecological Systems Theory (Bronfenbrenner, 1979) constitutes the theoretical framework for the study, focusing on how teachers’ risky play attitudes facilitate bidirectional interaction with children at the microsystem level. An explanatory sequential mixed method design was used. The quantitative portion included 484 preschool teachers who filled out the Scale for the Attitudes towards Risky Play at Early Childhood-Teacher Form. The qualitative part included semi-structured interviews with 21 preschool teachers. Participants were given informed consent prior to any procedure and the right to withdraw at any time. Pseudonyms have replaced the names of participants. Quantitative results revealed significant differences in teachers’ risky play attitudes in terms of preschool type, presence of teachers’ aides, and daily outdoor time. Qualitative results indicated teachers’ concerns in relation to parents and administrators. That’s, the way parents and administrators perceive risky play, either positive or negative, has an impact on teachers’ practices in allowing or prohibiting risky play outdoors. These findings suggest the need for professional training and continuous collaboration of teachers with parents and administrators in supporting risky play opportunities in school settings.