Most prisoners want to better themselves so that they never have to return to prison furthermore many studies have shown that the best way to reform and improve behaviour is through education however students studying in prison face numerous challenges in their endeavour to ameliorate themselves. In other words, schooling has become a painful experience for many of them and their feelings of shame and anger at becoming unsuccessful in a world where academic achievement is highly valued, run deep. Public perception is that prisoners should be denied access to educational opportunities and be punished for the crimes committed. Using qualitative phenomenological design, the article explores in detail the learning experiences of a group of inmates who are studying at undergraduate level, via distance learning. This article specifically focuses on the experiences and challenges encountered by these students. Data was collected from the five participants using semi-structured interviews and analysed using content analysis. All the participants were provided with informed consent and they demonstrated their willingness to participate in the research. Based on the data collected, we conclude that although the student inmates find the prison environment to impact negatively on their studies, they (students) also attach great value to their studies and hope to use it to secure employment once released from prison.