This research was motivated by my previous work as a pro bono counsellor in Uganda's prisons, during which time I found that prisoners had many needs that they claimed were not being met by the prison system. It was profoundly clear that so much goes on inside the prison walls that is unknown, as there is hardly any information other than what is written in the newspapers. This research is therefore an attempt to create insight into the experiences of prisoners and the efforts of the prison services to transit from a punitive to a correctional system. The research therefore delves into the policy and legal underpinnings of the prison service in Uganda, attempts to implement the policy, challenges experienced by both policy implementers and prisoners; and prospects for the future of prisons in Uganda. It is my hope that this research is a useful addition to the body of knowledge on correctional rehabilitation in not only Uganda and and East Africa, and the entire continent of Africa.