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According to the literature on desistance, the process of re-entering society after release from imprisonment is distinct from the process of desistance. Scholars have also acknowledged the existence of gendered differences in both reentry and desistance processes. Among the array of players in the lives of formerly incarcerated individuals, mentors have become an increasingly popular form of social support in post-incarceration programs—particularly for women in reentry. Given the increasing interest in mentoring programs, this study uses semi-structured interviews with mentors (N = 10) and clients (N = 11) in a women’s post-incarceration mentoring program to assess the role of mentors in the reentry process and the desistance process. It was found that mentors aid in these processes by serving as facilitators of change for women who are open to such change and by facilitating in their development of constructive long-term behaviors.