African prison writings began to emerge as a recognizable literary genre in the early twentieth century during colonial rule when imprisonment became widespread and institutionalized. Thus, the initial development of African prison writings is a manifestation of and a confrontation with European colonial modernity, which used the carceral system as a coercive instrument against restive populations. The further transmutations of this genre are inseparable from political developments on the continent. Although a few prison writings were written by white prisoners, it was when Western-educated blacks were incarcerated for anticolonial agitations that African prison writing emerged in the form of resistance literature. Ironically, many postcolonial African regimes imprisoned an evolving black intelligentsia and dissenters. They in turn wrote about their imprisonment and expressed their disillusionment with the excesses of African nationalist leaders, most of whom had experienced imprisonment by colonial authorities. Currently, prison literature has diverged from its early anticolonial and antipostcolonial political focus. It now includes writings by and about prisoners inspired by neoliberal notions of human rights and the idea that self-introspection manifested in confessional writing is therapeutic and can reduce recidivism. This chapter explores the origin, entrenchment, and the current spread of African prison writings.