In this chapter, we offer a reconsidered discourse to parental attitudes to children’s engagement with risky play. To do this, we applied Farley’s (1986) Type T “big thrill” and “small thrill” behaviours to parenting styles during children’s exposure to risky play. Our research project explored parents’ (N = 302) perceptions of a naturally inspired play park. We unpack the ways parents embraced a Middle T risk (middle thrill) parenting style. Despite the negative discourse around overprotective or helicopter parenting, we found most parents clearly understood and valued the importance of risk-taking in children’s lives. We posit that the majority of parents who visited a nature play park adopted a “middle thrill” parenting style regarding childhood risk-taking. By embracing a healthy risk appetite, parents actively encouraged their children to engage in calculated risks at the park. To provide a contrast to contemporary constructions of intensive parenting as overprotective and diluting risk, we outline a “sweet spot” of Middle T risk parenting. Parents employed appropriate and nuanced language to elucidate the myriad benefits the park offered regarding choice and risk-taking. These findings underscore the fact that parents clearly articulated their comprehension of the significance and merits associated with children to undertaking a middle level of risk-taking. This is foundational to building children’s risk literacy through embodied learning. The recent advent of the international standard—ISO 4980:2023 benefit–risk assessment for sports and recreational facilities, activities, and equipment—gives permission for parents to adopt Middle T risk-taking as an essential ingredient in play provision.