An increasingly popular gender-specific intervention to assist women involved in the criminal justice system (e.g., ex-prisoners) is mentoring. However, despite the growing popularity of mentoring, there is a dearth of literature that has explored the intervention’s efficacy, particularly as it relates to women involved in the criminal justice system. In the current study, client files of 64 women in a one-to-one mentoring program in Australia were examined to identify (a) the social and practical needs and obstacles faced by women overcoming their involvement with the justice system, and (b) the extent to which mentoring addressed these needs and obstacles. The results show that consistent with previous research, many of the women experienced a range of social and practical difficulties that impeded the desistance process. For a large portion of the women, however, mentoring helped overcome some difficulties by enhancing positive social capital in their lives. These findings are discussed in the context of how mentoring relationships can act as key turning points in the lives of women involved in the criminal justice system.