This work provides an insight into the philosophy of imprisonment for reform. For centuries now, the reform of the criminal has been one of the main objectives of imprisonment. This study questions the veracity of the power of imprisonment to reform criminals. There seem to be some inherent contradiction between the more we take criminals to prison, the rate of recidivism and the apparent threatening crime rate that we witness every day. This seems to negate if not dilute the assertion that imprisonment does reform criminals hence help in the fight against one of man''s worst enemies- crime.This work, therefore focuses on investigating whether the prison as we know it no matter how decent, civilized, big or small, new or old is capable of reforming criminals into responsible citizens.This work will be useful to ethicists, criminologists,lawyers, sociologists and anyone else interested in the correctional systems.