This chapter discusses smart mobility in sub-Saharan Africa to provide insights into (i) the history and relevance of smart mobility in its cities; (ii) empirical cases of smart mobility experiences in selected cities; and (iii) the potential of smart mobility in advancing urban planning reimagination in this region. Cities of South Africa were used as cases to demonstrate the importance of smart mobility in urban planning reimagination. Findings indicate that smart mobility is a new concept in sub-Saharan Africa and is in its nascent state. There are multiple barriers to smart mobility, including lack of integrated transportation, lack of investment by municipalities, lack of non-motorised transportation, the economic constraint of people, the demographic character and social and cultural behaviour of people. The cities also possess significant potential for the adoption of smart mobility. However, smart mobility might bring challenges to the built environment by influencing it through the transformation of the transportation system and urban spatial morphology. The resolution of the issues related to these two transformations remains vital for the creation of smart mobility and consequently smart cities. Therefore, urban planning should be reimagined for the transformation of the transportation system and the built form of the cities.