This thesis adds to the postcolonial perspective by using an empirically grounded analysis of the Caño Martín Peña Special Planning District to offer theoretical interventions. The case has recently been celebrated for combining a robust participatory practice and inventive planning strategies that “work with” the community. However, previous scholarship fails to underscore contextual specificity and the complexity of the process. Thus, I propose a critical methodology to engage with and highlight a systemic understanding of “informal” spaces. Following a multidimensional theoretical framework that converges around risk, situated knowledge, and design politics, this thesis reflects on three questions. (1) How can we improve the living conditions of residents in these areas without asking them to become part of the system that causes their “vulnerabilization”? (2) What is the appropriate scale to think about “working with ‘informality’”? (3) Are the “developmentalist” economic and political projects (capitalist, neoliberalist) the cause of “urban informality”? This thesis suggests that even “successful” participatory processes and sensitive projects are skewed by the politics behind government- approved practices that render the impacted populations legible, and technical documents that are incomprehensible to most. Additionally, I contrast the scale chosen for positive implementable infrastructure and design projects to alternative scales of administering policies that work with the continuous urbanization processes that lead to “informality.” The discussion brings forth how these processes were initially provoked by migration into cities due to imported industrialization operations. Finally, the thesis proposes a decentered and repoliticized framework to reflect on how “urban informality” is created, maintained, and perpetuated.