Over the past few decades, concerns about safety and liability have led to the elimination of features considered to be “risky” from many play environments. In response to this trend, some researchers are using a mix of a priori reasoning and empirical studies to make the case that risk is an integral part of challenging play, and that certain types of risky play are associated with health benefits and learning. New research and criticism of existing standards and research has encouraged the adoption of new regulatory language in the United Kingdom that acknowledges the value of risk in children’s play environments. This paper introduces the current debate over rethinking American play environments and playground standards to allow for beneficial risks. The authors presented on this topic at the Council of Educators in Landscape Architecture conference in March 2016 in an effort to engage academics and researchers in the field of landscape architecture. The paper reviews how concerns about safety and liability have and are influencing play environments in the United States. It critically examines the way that the U.S. Consumer Product Safety Commission collects data on injuries related to play environments and suggests a more holistic approach to collecting and reporting data is needed to inform regulatory and design decisions. Finally, it discusses how landscape architecture academics may contribute to policy debates about risk in play environments, through research and participatory design studios. Some opportunities for future research are discussed.