This paper examines the role that cities play for the enforcement of social rights in the South, through an empirical study of the outcomes of a landmark dialogical justice case of the Colombian Court: the waste pickers' case (T- 291/09). This case sought to ensure livelihoods for hundreds of waste pickers affected by the closure of the major dump in Cali, ordering municipal authorities to design a public policy on waste-pickers through a participatory process involving different actors. Although the paper defends dialogical justice approaches, it also illustrates its working challenges at the municipal level. The waste pickers' case presents a story of limited enforcement, backlash, capturing of the waste pickers' voices and, in general, of the inability of the Court to mediate the 'dialogue' among stakeholders. By contrasting the waste pickers' case to other cases, the paper draws attention to overlooked challenges that are present in intermediate cities for SERs enforcement.