The notion of contrapuntal urbanism refers to how individual factors work together to create a coherent (but not necessarily unitary) urban system which may be in a state of flux. With specific reference to urban housing for the poor, a plethora of factors may interact in various ways to configure the efficiency of its delivery. The situation is prevalent within the Southern African region in former colonial and apartheid societies such as South Africa and Namibia. This proposed chapter seeks to assess the implications of interconnected factors for urban housing delivery for the poor in the informal settlements of Namibia. The choice of Namibia has been informed by the relatively less focus on this country in the extant academic literature on urban housing delivery. The largely qualitative study relies on document and discourse analyses, as well as interviews to make its arguments. The research dissects cases of both successful and less successful models of housing delivery for the poor in Namibia’s informal settlements. For successful models of housing delivery, factors such as housing financing and cooperative production systems interact to ensure an increase in supply. And for less successful models of housing delivery for the poor, postcolonial dynamics such as land use regulations and rural–urban migration are important interacting factors. The chapter concludes by proposing a postcolonial relational schema to ensure improved urban housing delivery for the poor in these settlements. The model prioritises interventions such as private non-commercial, cooperative and public sector housing production systems, as well as reforms in institutional and policy frameworks.