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The Pennsylvania Prison Society’s Building Connection reentry workshops support incarcerated individuals preparing for reintegration by fostering mentorship, emotional support, and practical reentry skills. This study provides an external review of the program to evaluate its effectiveness, identify key components, and offer recommendations for expansion. Using qualitative methods, data collection included in-person program observations, interviews with post-release participants, surveys of incarcerated participants, and discussions with program staff. Findings highlight five core program strengths: (1) the creation of a supportive and open discussion space, (2) facilitators' relatability and sincerity, (3) the use of real-world scenarios, (4) group-based peer learning, and (5) long-term post-release support. Participants reported increased self-confidence, improved communication skills, greater awareness of available reentry resources, and stronger social support networks. Analysis demonstrates that Building Connection aligns with evidence-based reentry practices, particularly through its balance of emotional and instrumental support, pre-release mentor matching, and a continuum of care facilitated by an external organization. The findings suggest that the program is an effective model for fostering reentry success and should be expanded to additional correctional facilities. Future research should examine long-term outcomes to further assess the program’s impact on recidivism and post-release stability.