This article explores the encounter between parkour as an unstructured and culturally innovative practice, challenging both physical as well as organisational spaces, and UISP (Unione Italiana Sport per Tutti/Italian Union of Sport for All) as a sport-promotion body open to organisational and cultural experimentation. Drawing on a multi-method qualitative approach (analysis of documentary material, interviews and focus groups), it looks at the role of UISP in the diffusion and legitimisation of parkour within the Italian context, investigating the interplay between the cultural and organisational logics of both this new practice itself on the one hand, and the organisations that are trying to accommodate it on the other. The incorporation in a sport-for-all organisation like UISP provides traceurs with a safe and legitimised space, which is, however, ‘loose’ enough to maintain the fluidity of the practice. Nonetheless, by enabling the coexistence of different and competing definitions and uses of parkour, this fluid organisational space reproduces tensions among traceurs and weakens their voice in UISP's decision-making processes.