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Ex-offenders face many challenges and barriers in obtaining sustainable employment when reentering society. Researchers have demonstrated that participation in a work release program prior to release from prison may be beneficial. However, not all work release reentry programs are alike. Because offenders are the benefactors of these programs, it is essential their experiences are captured. The purpose of this phenomenological study was to understand and describe unique experiences of male ex-offenders previously assigned to a work release program in an urban setting in an Atlantic East Coast state. Bronfenbrenner's ecological systems theory framed the study. This study gives voice to and provides an understanding of the experiences of 5 individuals recruited utilizing the snowball method who were seeking employment while in the work release program. Data was analyzed using Moustakas' 7-step data analysis procedure. Findings may inform program and policy makers of the importance to provide a more robust work release program that includes job readiness support and resources and the need to establish a partnership with local employers. Four themes emerged including: (a) Lack of Resources, (b) Need for Outside Support System, (c) Perception of Lack of Empathy from Correctional Officers and Employers, and (d) Gratitude and Appreciation to Participate in the Work Release Program. Findings further support the importance of collaboration between the criminal justice system, transitional reentry programs and employers in order to achieve positive social change with successful outcomes. These findings may lead to a reinvestment of resources and restructuring of reentry programs to serve its beneficiaries.