This essay aims to engage, mainly from theoretical perspectives with analytical eclecticism, a historical and contemporary analysis of African educational and social developmental contexts. It relays the real colonial connections that are still attached to this context. The essay relates the historical location as well as the socio-cultural embeddedness of the African philosophy of Ubuntu, which may have indirectly facilitated the initial entry of colonialism. It critically locates the thick philosophical and epistemological problematics that have previously and again, post-factually limited the foundational reconstructions, and by extension, the relevance of Africa’s learning and related possibilities for achieving social well-being. At the end, the essay calls for the urgent decolonization of Africa’s philosophies and epistemologies of education, so that learning contexts can aid the now non-delinkable desires, indeed, needs for social development.