Academic debates on union politics in the Global South have tended to focus on effective union and solidarity campaigns. Labour struggles, however, do not always yield beneficial outcomes for workers. Three decades of neo-liberal policies in Sri Lanka suggests complexities that labour rights advocates would potentially prefer to shy away from. Efforts to re-politicize union rights of labour in an era of economic liberalization require us to sharpen our gaze on these ruptures too. Using workplace ethnography in Sri Lanka, this article details the interactions of management and labour during a struggle over union formation. It suggests that paying detailed attention to the political economy of labour highlights a complex situation in which fostering unionization, despite its importance for the collective will of labour, may require hard work.