As a consequence of neoliberalism, employment has become increasingly precarious and informal, sitting outside of traditional organizational contexts. There is a need to better understand how these structures emerge and, importantly, how workers can also adapt to challenge these shifts. This article is a study of a labour dispute between Philadelphia taxicab drivers and the governmental regulatory body. The dispute was centred around the implementation of surveillance technologies to regulate and control the industry and the drivers’ working practices which they considered to be de-professionalizing and an infringement of their liberty. The drivers resisted through traditional organizing, legal challenges and creating unconventional alliances. We argue that this labour dispute should be seen in the wider context of how a neoliberal political economy emerges and is maintained – in this case not by capital, but by the state. The article is a longitudinal case study covering the period from 2004 to 2011. As such, it is a prologue to later technologically driven transformations in the taxicab industry (such as ride-hailing apps) that have further exacerbated precarity among the workforce.