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Cycling is a key mobility option for low-income citizens in the Global South. In India, cycling is a socio-technical regime that is undergoing substantial transition, driven by diverse visions of sustainable mobility held by actors and contrasting strategies undertaken by them. In the course of the transitions, top-down policies and planning initiatives dictate the directions of transitions by enabling or constraining user routines. Such is the case in Kolkata, a megacity in India. We studied the multi-faceted nature of transitions in the cycling regime in Kolkata, focusing on the intersection of administrative practices, socio-institutional practices, users’ roles and discourses around cycling. Applying these concepts, we examined the processes of banning cycling and implementation of cycle sharing in the city. We observed that users’ roles varied significantly across the two trajectories of change. Their influence in shaping transitions …