The provision of education that is both effective and relevant to the needs of students within prison is challenging on a number of levels. The uniqueness of prison culture with a regime characterised by a focus on security measures such as lock-downs and head counts constrains the possibilities for learning. The absence of a supportive learning environment together with an emphasis on punishment rather than rehabilitation has the effect of marginalising education in prison so that ‘education’ has come to be seen by some as ‘off limits’. Education in basic skills such as literacy and numeracy that contributes to ‘life skills’ is given priority. In contrast, access to higher education is more problematic with this generally perceived by both prisoners and prison staff as an ‘elite’ activity. This article adopts a case study approach to consider the barriers to higher education distance learning in the prison setting. It focuses on the practical and organisational constraints faced by educators in their efforts to help students in prison negotiate the different worlds of prison and higher education. It also highlights the value of one-to-one tutorial support in facilitating learning in less than optimum teaching conditions.