Risky play, accompanied by thrilling feelings with real or perceived risks, is beneficial for children's development. Playground quality and teachers' attitudes about risk can influence preschoolers' risky play opportunities. In this study, 10 U.S. preschools' outdoor environments were rated using the Seven Cs Scale. Playgrounds scored lowest in challenge, demonstrating a lack of risky play opportunities and highest in context and connectivity, exhibiting adequate safety measures and pathways. The Tolerance for Risk in Play Scale was used to assess 58 teachers' attitudes. The average score was 29 (on a scale of 0 to 100, highest risk tolerance). Across risky play categories, teachers were most accepting of rough-and-tumble play and least accepting of play with dangerous tools. During a focus group, teachers also expressed concerns regarding overly restrictive safety regulations. The findings highlight the need for further teacher education concerning risky play.