This paper examines two bikeshare programs implemented in two Global South cities, examining the role of users in promoting sustainable transport. To explore the sustainability of smart cycling, we argue that it is important to understand the prevailing administrative and socio-institutional practices within a given context. For the effective stabilisation of smart regimes, harmony between the administrative and socio-institutional practices must be established. In this context, we introduce a complementary approach to understanding transitions. Maintenance of political commitments and institutional support are crucial for cycling success, not incidental footloose initiatives. We explore two case studies in the context of the Global South, in the first one top-down policies and planning initiatives dictate the directions of transitions by enabling or constraining user routines. In the second one, citizens take control to resolve a transport deficit by initiating and driving a very bottom-up user-led transition narrative. We propose a framework to cater to the unique political, cultural and smart discourses of the Global South and the role of users in conjunction with the administrative and socio-institutional practices around them. Investigating both the bikeshare cases through the lens of this framework provides unique insights extending our knowledge beyond the built environment features of sustainable planning initiatives. Our findings reveal the complex narratives that are in play in developing nations and conclude that understanding and realising cycling transitions in southern megacities require a different approach compared to the Global North.