This paper examines the interrelationship between law and lifestyle sports, viewed through the lens of parkour. We argue that the literature relating to legal approaches to lifestyle sport is currently underdeveloped. Law is viewed as a largely negative presence, seen particularly in terms of the ways in which counter-cultural activities are policed and regulated, where such activities are perceived to be transgressive and undesirable. We argue that this is a somewhat unsophisticated take on how the law can operate, with law constructed as an outcome of constraints to behaviour (where the law authorises or prohibits), distinct from the legal contexts, environments and spaces in which these relationships occur. We examine specifically the interrelationship between risk and benefit and how the law recognises issues of social utility or value, particularly within the context of lifestyle sport. A case study is provided of the employment of claims to social value present in the advancing institutionalisation of parkour in the United Kingdom. Through the case study, the paper seeks to foreground a more nuanced position that moves away from user-centred constructions of law as an imposition toward an appreciation of how the law can be used to support and extend claims to space.