This article focuses on the educational life histories of nine prisoner learners aged between 18 and 21 years which were collated as part of doctoral work which sought to access the life histories of adult male prisoners who were attending a prison school while incarcerated in prison. The nine life histories of the young men were collated not only in two Dublin prison sites: St. Patrick's Institution (mainly) but also Mountjoy Prison and their educational life histories are explored in this article with the specific aim of offering insights into young adult male prisoner learners' experiences of education. Negative experiences of compulsory education were reported by the nine prisoner learners interviewed, none of whom had completed upper second level education. The average age of the young adults was 19 years. Two had no experience of secondary school education and six of the nine reported being expelled from school. The intergenerational impact of imprisonment and cycle of disadvantage was illustrated across many of the life history interviews. Prisoner learners reported having experienced stressful events in their childhood, events which included, inter alia, the separation of parents, being removed from parental care and witnessing alcohol and drug misuse and violence in the home. Two of the prisoner learners reported learning to read and write in the prison school and a profile of one prisoner learner, Nick, aged 20, is included in this article.