This dissertation explores the dynamics of workers’ collective political engagement through organized labour in an authoritarian environment and a regime in transition. While the literature on social movements and organized labour in the Middle East and North Africa (MENA) has captured the characteristics and impact of repression and corporatist systems on a union structure and elite strategies, this research contributes to a body of work that position the activities, networks and calculations of unionized workers at the centre of analysis. Using the Tunisian General Labour Union as an in-depth case-study, it will show that to fully comprehend the important role of a labour union as a vehicle for political engagement, one must pay close attention to the networks, strategies, and tactics of its militant base. By adopting a conceptual framework that gives attention to interactions of structures and agents, and therefore not privileging one over the other, it shows how in a region in which unions were conventionally labelled as “inconsequential” and “empty shells,” unionized workers, particularly those belonging to more militant sectors, have repeatedly seized on their personal networks and relationships, while drawing on systems of meaning making and shared collective memory to engage in various forms of activism. By doing so, it underscores the limitations of cooptation as a political strategy for ensuring obedience and compliance. Moreover, to better understand workers’ activism and political engagement in MENA, this dissertation calls for a change in how “successful mobilization” is measured and assessed. In particular, it draws attention to the objectives and goals of workers’ collective action, aims that cannot always be equated with the pursuit of a standardized path to democracy developed largely by institutions located in the West.