Although this exploratory research was conducted with a small sample of mentors (n=11) and mentees (n=14), some themes emerged. The findings suggest that, with the proper support, both mentors and mentees can benefit from the mentoring relationship so that reintegration is facilitated. If mentors are prepared for realistic expectations for young adult offenders just released from incarceration, disappointment and frustrations among mentors can be mitigated. Poor relationships with individual mentees do not necessarily produce dissatisfaction with the overall mentoring experience if preparatory training confronts difficulties that can emerge in mentoring interactions. The distinctive role of the mentor in successful reintegration is the provision of a personal relationship whose focus is on guiding the mentee through the difficult process of reintegration. This means that mentoring is most effective when both mentors and mentees establish a trusting relationship that involves mutual respect and empathy. The Syracuse-based Self-Development Reentry Program is managed by the Center for Community Alternatives. Its aim is to assist young adults between the ages of 16 and 24 who have some indication of substance abuse and are returning to the community after incarceration. Upon release, participants are eligible to receive various services, including substance abuse treatment readiness and treatment-related services, case management, employment services, and mentoring. The research was conducted in the winter and spring of 2007 and involved researcher observation of mentor training and meetings, a satisfaction survey for mentors and mentees, and interviews with mentors and mentees. 3 references