Latin American constitutions recognize several social rights (SR). But the gap between SR’s declaration and implementation is significant. People resorted to courts to seek remedies for unfulfilled SR, often targeting structural problems. While courts were receptive to such claims, the enforcement of complex decisions faces challenges that remain under-explored. The paper claims that a way to navigate enforcement hurdles is to craft “experimentalist” remedies and monitoring mechanisms. As experimentalism promotes participation, decentralization and experience-based learning, it can help contextualize SR and address judges’ limitations to engage in policy issues. The paper presents a detailed research of a landmark environmental litigation in Argentina directed at cleaning a massive river basin. Because of contamination, people living in slums in riverbanks had to be relocated. Relocations triggered promising experimentalist innovations in case-management and policymaking.