This chapter invites scholars to pay attention to the role that cities play in the enforcement of social economic rights (SERs), focusing on a type of decisions that some authors have called judicial experimentalism. Experimental justice refers to a judicial approach through which the courts, rather than rendering a final resolution on a case, pursue solutions through the promotion of dialogue and negotiation between governments and affected populations. Gathering insights from socio-legal studies, legal geography and critical urbanism, the chapter proposes an interdisciplinary framework for analysis and a set of research questions that could aid experimental scholars in broadening their research agendas in order to understand the limits and possibilities of SERs structural cases in the global South.