This chapter explores the role, success and failures of spatial planning in shaping African cities and its influence on livelihoods. To date, planning in Africa has largely failed to address the needs and livelihoods of the poor and struggled to address wider issues such as spatial and economic inclusion, health inequalities, future pandemics and climate change. Planning for sustainable livelihoods across Africa must consider the distinction between universal or more generic approaches to planning and the experience of particular places and people, specifically, accounting for the needs and practices of informal entrepreneurs. This chapter first explores how the legacy of colonial planning has impacted the segregation of spaces and hence of livelihoods, particularly those of the poorer communities. It then discusses the barriers faced by planning to address the informal nature of the livelihoods of lower-income communities. Finally, it sketches out the challenges that need to be overcome and how planning for sustainable livelihoods should thus be tackled in Africa in the future.