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Children's risky play opportunities depend on supervising adults' attitudes and the play environment. The possibilities to engage in risk-taking outdoor play for children have seriously decreased over the last few decades, due to safety concerns and adults' preoccupation with protection. In response to this shift, research has increasingly focused on influencing factors on professional attitudes toward risk-taking in children's play. However, children's perspective on risky play is underrepresented in the recent literature. This study generates awareness of children's risky play preferences and interests to help professional caretakers hone their facilitating role. We explored children's notions of risk and challenge in play during a loose parts intervention stimulating risky play and facilitated by after-school childcare practitioners. A thematic analysis examined observations, informal conversations, and roundtable talks with children about their risky play experiences. Children describe their risk-taking in play as experimental and daring. The findings report on children's general views on risky play, their play experiences with loose parts, their real-life risky play experiences, and their opinions on the role of practitioners. By relating the results to risky play research and self-determination theory, this study offers insight into children's innate needs. Taking risks on their own terms gives children a sense of self-confidence and mastery, and forces them into new relationships with other children and guiding adults. Consequently, children fulfill the three universal needs of self-determination theory: autonomy, competence, and relatedness.