Parole hearings offer hope of leaving prison early and returning to one’s community. Preparing for the hearing is an important endeavor for incarcerated individuals, but information about how to effectively prepare and what to include in a parole packet is often lacking. Further, once granted parole, individuals face multiple challenges during the reentry transition. Despite the need for support and information, few comprehensive resources exist, leaving individuals to navigate complex situations on their own. In 2021, a unique program called PREPARE was launched in Maryland to assist clients with all aspects of parole preparation from packet creation to reentry planning. This qualitative case study offers a description of the PREPARE program informed by review of program documents and interviews with three program advocates. Thematic analysis was used to evaluate data from interviews with six formerly incarcerated women about their experiences working with PREPARE advocates. Findings yielded four main themes: the importance of receiving accurate information, the impact of being treated with respect, the ways feeling prepared for parole hearings increased self-confidence, and the challenges of securing employment and housing upon reentry even with support. This study contributes to the literature on justice-involved women by offering firsthand perspectives from clients involved with an innovative program about what is needed during the parole and reentry process. Having access to accurate information, receiving compassionate support, and on-going connection to advocates were identified as factors supporting success. Clinical implications for social work practice with justice-involved clients focused on empowerment and self-determination are discussed.