How individuals incarcerated in the Global South engage with the official rehabilitative model remains largely under-documented. Through analysis of the narratives of men and women living in a large, medium-security correctional complex in Gauteng, South Africa, I argue that the grandiloquent official discourse of rehabilitation constitutes an important resource for those incarcerated. Highlighting the importance of local context in debates about carceral rehabilitation, I demonstrate that not only prisoners’ personal circumstances, but also the wider socio-economic context of enduring colonial legacies of structural inequalities shape their interactions with the penal regime. By foregrounding what those subjected to penal power make of their incarceration, I argue that the official rehabilitative discourse helps many to make sense of their predicament, actualise their lives, and sustain hope. I highlight how individual narrative strategies are channeled by and mapped on the official discourse of rehabilitation, free will, and personal responsibility, attesting to the success of the disciplinary project of the post-apartheid prison. I demonstrate how prisoners incorporate engagement with the rehabilitative model into a moral order of carceral cohabitation. I suggest that narrative work in the prison constitutes a nexus of individual needs and private aspirations and structural regimes of inequality, poverty, deprivation, and neglect.