This article looks at the environment that past offenders meet in the society once they are released and the difference in prison life and the life of freedom and the difficulties they meet as they try to adjust to the new life. This article critically studies some of the major issues facing the re-entry policy. These issues include:  1. Almost all convicts who are released per annum more than half of them will commit crimes and get rearrested again.  2. The prison rates are still increasing resulting in over population on the current prisons  3. Due to the increase in crime and criminals themselves, the criminal justice system and the re-entry program is being strained by it.  4. The importance of the re-entry program and the challenges faced by the convicts as they try to get integrated into the society is not fully understood by the society and the justice system.  5. The state cannot afford to offer vocational training to all offenders as some are rebellious to the program.  6. The success that has resulted from the implantation of the program.  7. Some of the changes that should be brought into the system.  8. Judiciary should play a role in the program. Prison re-entry is the use of various types of programs aimed at reintegrating past offenders into the society once they have served their sentence and released. Prisoner re-entry has become a major issue for the government resulting in a prisoner re-entry policy which was created to look after the issue of released prisoners. In each year, approximately 700,000 prisoners are released from the prisons whereby 70 percent end up getting rearrested and sent back to the prisons again. In addition, the released prisoners end up committing more crimes, a fact that has resulted in an increase of crimes all over the country and an increase of the prison population to very high numbers The reason for this has been due to unsuccessful re-entry processes of the convicts into the society. Therefore for the policy to be successful, the policy should ensure that there is all-inclusive case management analyses whereby it shall enable the offender acquire new economical skills in order to be able to be dependent on his own while at the same time being a law abiding citizen. Due to the difficulties they face once they are released back into the society, there are numerous programs available which enable the transition from prison to freedom be a smooth one. Some of the programs involve, drug rehabilitation, vocational training and pre and post release programs, each designed to cater for the various different crimes and individual. In addition, the government has created re-entry courts which have been designed to offer very intensive management and treatment of the offenders that starts at the initial stage when the offender is sentenced. The courts have also assisted in the management of the offenders’ behaviour, whereby the offender is made accountable for his actions and assisted in reconciling his behaviour to the expected norms of the society. However, the parole department is underfunded and therefore it cannot deliver on its mandate and as a result, making it more of a legal entity than an organized procedure or reintegrating prisoners back to the society. Due to the challe