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Informal workers are commonly understood to operate “outside of” – or even at odds with – the legal system. Yet as informal workers have become more visible as collective political actors over the past decade, so too has the complexity of their position vis-à-vis the state and the legal system become more evident. For instance, while informal workers are excluded from certain legal domains, they and their organizations also use legal systems in a variety of ways. This paper traces two cases of legal transformation in which the efforts of informal workers’ organizations shifted the national legal infrastructure toward state-sanctioned recognition of informal work as legitimate work—thus upending decades of exclusion from resources critical to informal livelihoods. In Colombia, the Asociación de Recicladores de Bogotá (ARB), a waste pickers’ organization, used litigation to gain inclusion in – to operate as part of – the city’s solid waste management system. In India, the Self-Employed Women’s Association (SEWA) used litigation to gain access to public space and livelihood rights for street vendors. While the ultimate outcome is similar in the two cases, they differ on the nature of inclusion: Colombia’s informal waste pickers gained structural inclusion into a municipal system, whereas India’s street vendors gained contingent inclusion into urban economies. The two-case comparison enables us both to identify the conditions in common that led to legal transformation, and to isolate the distinct mechanisms that led to different terms of inclusion.