Risky play is invigorating, challenging play with uncertain outcomes that optimizes children's development, health, and everyday well-being and creates opportunities to develop decision-making skills in low-consequence contexts, experience positive feelings such as confidence and courage, and enjoy health-promoting physical activity. Children with disabilities have fewer opportunities to engage in risky play, often because of the intervention of well-intentioned adults. In this paper, we define and examine the benefits of risky play for children with and without disabilities. Then, we examine the role of caregivers in “gatekeeping” risky play opportunities. We present two novel instruments that allow practitioners to assess caregivers' tolerance of risky play: the Tolerance of Risk in Play Scale-Revised (TRiPS-R) and the Tolerance of Risk in Play Scale-Teacher (T-TRiPS). We describe the results of psychometric analyses of these instruments, demonstrating evidence for construct validity and internal reliability of data collected using these instruments. Finally, we encourage practitioners who work with children with disabilities to employ these tools to promote risky play for the children they serve.