Along with other countries around the world, South Africa is currently faced with the need for informal settlement upgrading through regeneration programmes. The South African Government since 1994 has initiated and implemented several housing delivery programmes and subsidy mechanisms to eliminate the incidence of ‘slum housing’ and its associated poverty. In addition to high levels of unemployment, there is also a widely acknowledged need for housing and municipal infrastructure (water supply, sewerage, streets, stormwater drainage, electricity, and refuse collection). Provision of adequate housing and infrastructure for the poor to reduce poverty and improve the quality of people’s lives has been a huge challenge for the South African Government over the years. The high level of unemployment and relatively low average wage level contribute to a major housing affordability problem in South Africa. The high unemployment rate forces many people to live in unstructured settlements; hence the need for housing-and infrastructure-led regeneration. Urban regeneration has become a critical concern for the South African Government. The aim of this chapter is to raise questions about housing-and infrastructure-led regeneration through the upgrading and eradication of informal settlements in South Africa. The chapter investigates the lessons and challenges that can be learnt through housing-and infrastructure-led regeneration programmes in two South African municipalities. The chapter closes with recommendations on how housing and infrastructure led regeneration can be improved.