In this chapter, I draw heavily on my experience as Social Development Manager on the Inner-City Housing Project, implemented by the National Housing Trust in Jamaica. This experience provided vivid-to-examples of the profound challenges inherent in implementing the national housing policy. Using social housing as a case study, I explore how the legacies of class privilege, the deeply personal nature of policymaking and the quest for developmental approaches intersect in postcolonial bureaucracies. This essay highlights the enduring post-emancipation demand for shelter across diverse sections of Jamaica’s urban poor. The complex socio-economic and cultural pressures that have rendered social housing a policy imperative are highlighted as obstacles to sustainable futures. Finally, the essay explores the ways in which sexism, racism, political patronage and other factors of disadvantage converge to create deeply rooted obstacles to policy objectives.