This article examines the persistent gender gap in parkour by analysing women experiences and meanings of security and insecurity within indoor and outdoor, formal and informal environments in the context of Spanish parkour institutionalisation. Drawing on qualitative ethnographic research conducted in Spain between 2024 and 2025, this study reveals the complex assemblages of bodies, materialities, discourses, emotions, spaces and gender norms in which discrimination and resistance emerge. Although the literature suggests that indoor, formal spaces derived from institutionalisation serve as avenues for greater inclusion, the findings stress that this process could reproduce gender discrimination at spatial and discursive levels. Spatially, institutional environments may reduce women’s insecurity but do not necessarily lead to greater participation in outdoor informal settings, reinforcing gendered public/private divisions. Discursively, it sparks debates about the loss of authenticity of the discipline and its inherent inclusive character, highlighting an overlooked intersection to date. Nevertheless, by attending to the embodied, dynamic and contested character of social reality, the findings also show how women create spaces of belonging and contestation inside and outside institutionalisation. Overall, the study contributes to broader social science debates by offering insights into gender inequalities and advocating for dynamic, non-dichotomous approaches to the study of space, sport, leisure and social inclusion.