With the growing discourse on the role of physical education in promoting physical literacy an important question remains largely unanswered; What skills and knowledge do students take from their physical education experiences and choose to enact in their leisure time? In examining the goals for physical education across the globe it becomes clear that as a discipline we have gladly assumed this transfer to be positive. Recent work by my collaborators and I (e.g. Knowles, Wallhead & Readdy, 2018) and Peter Iserbyt and his graduate students suggests that this transfer of motives and participation from PE to an extra-curricular school physical activity context is complex and challenging to predict. Using a variety of different curriculum interventions including Sport Education, Parkour and group-based fitness (crossfit) our work has shown that even when the PE curricular experience is motivating and engaging to the students, their choice to participate is confounded by multiple barriers within the extra-curricular context. Using behavioural and motivational lenses, we have found that the extra-curricular PA context needs to be carefully designed to facilitate participation. Within Elementary schools this can include having the environment and equipment similar to the PE context, providing choice to the level of competition embedded in the extra-curricular context and providing a broader scope of activities that include both individual and team sports. Within secondary schools, this challenge seems to grow as the culture and structure of schools institutionalize either being sedentary, or only being active if they are ‘training’ for a sport. Providing rewards for group participation and making these extra-curricular fitness activities attractive to the less active students can promote transfer within high school contexts. Significant challenges remain and future research is needed to design extra-curricular physical activity contexts that appeal to a broader group of students.