This article offers a unique reflection on teaching methods which engaged some of the most disaffected learners in a program of learning to build essential skills of literacy and numeracy. Several successes have been documented. The development of a social learning space and the formation of learning networks are just some of the factors which engaged learners. The use of information communications technology (ICT) to develop interest and motivation is also significant. These findings feed into the wider debate on widening participation and lifelong learning. This article also highlights some of the key tensions in delivering successful learning in a closed custodial establishment. The Northern Ireland Prison Service serves the community by keeping in secure, safe, and humane custody those committed by the courts, and by working with prisoners and with organizations seeking to reduce the risk of reoffending. This article presents a personal account of teaching based on 6 years of experience working in Maghaberry Prison in Northern Ireland. Successful teaching approaches, as well as practical inconveniences faced daily by educationalists working in this environment are presented. References