Contemporary environmental crises are often attributable to a growing disconnect between humans and the natural world. One potential solution to this disconnect, as it relates to children, is the naturalizing of school playgrounds. This paper seeks to contextualize the impacts of a school ground naturalization program on the outdoor play and learning ecosystem. Drawing on results of a collaborative and qualitative case study, this paper highlights the ability of an outdoor play and learning spaces program to induce a culture shift toward the endorsement and advocacy of outdoor play and learning among school communities, catalyzing a need for supporting policy and regulation.