The increasing popularity of action and lifestyle sports (e.g. skateboarding, parkour, BMX, mountain biking, and snowboarding) has been recognised as an important trend in youth lifestyles. In contrast to traditional sports, these activities are individualistic, lack rules, and have celebrated anti-authoritarian, 'do-it-yourself' and anti-competition cultural values. Athlete learning in action sport is also largely informal and self-regulated, with peer-to-peer learning dominating and digital technologies playing a central role. However, lifestyle sports are becoming increasingly popular for youth development, including in institutionalised settings and PE curricula. With the increasing professionalisation of some action sports including in international competitions such as the Olympics, there is an increased focus on coaching, with funding directed to coach development and increasing numbers of athletes in structured training programmes. This chapter explores this changing landscape of action and lifestyle youth sports cultures. In so doing, it critically discusses the challenges and opportunities for coaching. First, it outlines the dominance of informal learning environments in lifestyle sports, including the use of digital technologies. Second, it considers coaching and learning in more structured environments, which often differs in ethos and approach to many traditional sporting cultures. Drawing on sociocultural views of learning the chapter shows how disrupting the ‘adult as expert’ can create less hierarchical and more equitable learning environments. However, coaches being absent from learning environments also has potential implications for safety management and young athlete welfare. Lasty, it outlines future directions and considerations in coaching research and policy/practice.