Violent crimes in Jamaica continue to increase and are disproportionately committed by unskilled males from inner-city communities. Local research describes Jamaica’s correctional system as predominately “punitive.” Despite significant international research on desistance from crime and re/integration into society, Jamaica’s criminal justice policies have yet to reflect these findings. Furthermore, prisoner re-entry frameworks, developed from international research contexts have not captured how the prisoner re-entry narrative influences and affects each stage of the prisoner re-entry process. This chapter proposes a strength-based, holistic model and approach to the prisoner re-entry process in Jamaica based on international research.