Cities have revived a tendency to look to other cities in a conscious attempt to learn, adapt or adopt innovative practices in the field of urban planning and development. Much has been published on how such cities learn from each other in the global North, as well as some in Latin America and Asia, but little empirical research is available relating to sub-Saharan Africa. As a result, not much is known about the perception of practitioners in this part of the world, of prevailing international learning nomenclature, or of their understanding and interpretation of the dynamics of associated complex learning processes. This article focuses on a case study of the international United Cities and Local Governments (UCLG) “mentorship programme” involving the eThekwini Municipality in Durban, South Africa, and the cities of Otjiwarongo in Namibia and Mzuzu in Malawi. Instead of a single, unified and coherent conceptualisation of city-to-city learning, the study unearthed a messy and complex picture of multiple understandings of this concept among learning stakeholders. Crucially, it exposed strong resistance from African practitioners to the UCLG learning terminology of “city mentorship”, yielding a call to policy-makers for greater sensitivity about definitions of key constructs. Whilst making the case for city-to-city learning, it provides new insights that can contribute to more nuanced understandings of the complexity and the politics of knowledge transfer among cities.