Despite having some of the strongest protections for temporary workers in the nation, Chicago is no exception to the patterns of wage theft, workplace injuries, and rights violations prevalent in U.S. temporary work. Critical analyses of the practices and policies of organizations are largely absent from the literature, even though worker centers, attorneys, and the Illinois Department of Labor are involved in every aspect of temporary worker policy. This paper considers the challenges of the temporary workers’ rights movement from an organizational perspective. Data comes from in-depth, qualitative interviews with key informants at worker centers, legal institutions, and the IDOL. Informants provide insight into the organizational landscape surrounding temporary work in Chicago and the factors that contribute to the disconnect between policy and reality. In the face of these challenges, cooperation between organizations becomes critical. I conclude with recommendations to facilitate organizational cooperation and to address the specific failings of temporary worker policy in Chicago.