This study aims to compare parents' approaches in nature-based preschools in Turkey and Germany to identify similarities and differences and, thus, to understand risky play better. This research, planned as a cross-cultural study, was conducted as a multiple case study, one of the qualitative research designs. For this purpose, one nature-based preschool from Turkey and one from Germany were selected through purposive sampling. Fourteen parents from Turkey and 11 parents from Germany participated in the study. Data were collected through interviews. The research found that parents might create some barriers to risky play. Parents' concerns, supervision, overprotective attitudes, and lack of space and time were the factors that prevented risky play. Furthermore, parents' reactions and roles in the play were also analysed regarding their effects on risky play. According to the findings, the most common emotion experienced by parents during risky play was anxiety. German parents frequently stopped or terminated the play and made explanations, while Turkish parents often preferred the role of warning and not allowing children. The findings were discussed in the light of the literature, and conclusions were drawn.