Initially, we explore the global environment for Indigenous peoples who have experienced colonisation. We focus specifically on the over-representation of Indigenous peoples in custody and the inability ofthe prison system to facilitate ‘true rehabilitation’. This is starkly evident in the life of one of our students for example who at the age of 37 has spent all but 2 years of his adult life behind the razor wire. We then examine the Australian Indigenous story and the issues which contribute to the tragedy of institutionalisation. Constructed and reinforced by their custodial environment, our research examines seven stories from incarcerated Indigenous men and the impacts of low socio-economic background which conspired to influence their education journeys. Finally, this paper outlines a university initiative for education in prison for Australian Indigenous students and the glimpse it offers of an alternate reality within a system of failure. We think (as a society) that we want ‘rehabilitation’ but the sad irony for prisoners, is the destruction of the very things society values. Instead, the prison context is one which nurtures cruelty, violence, feelings of worthlessness, isolation and dependency (Judge Challeen, 1994 cited in Matthews, 2003, n.p.). Is this the pattern we want to continue globally through the 21st century? Can education be genuinely championed in our prison systems allowing inmates to gain the tools to intervene in and break the offending cycle?