Self-tracking technologies are now a taken-for-granted part of the road cyclist’s kit. We are interested in the gendered dynamics of one particular self-tracking platform: Strava. This article offers the concept of the cycling assemblage to explore how gendered subjectivities are felt and gain legitimacy on-the-move through the ongoing negotiated relationship between cycling bodies and technology. Our account draws on a cycling ethnography conducted with 27 Australian participants. Four vignettes demonstrate how Strava’s incorporation within road cycling assemblages functions as a mechanism of gendered inclusion and exclusion. We point toward the tensions of Strava as site of excess, where the pleasures and pains of the “quantified cycling self” may reinforce or challenge bodily and spatial boundaries associated with sporting masculine subjectivities and alternative femininities. A focus on cycling assemblages enhances our understanding of the spatiality, fragility, vitality, and multiplicity of gender-on-the-move.