Purpose: The purpose of this study is to measure the effect that age has on women’s gendered prisoner reentry experiences and the likelihood of desisting from crime and substance abuse. This study also seeks to evaluate the applicability of Paternoster and Bushway’s (2009) Identity Theory of Desistance (ITD) for a contemporary, all-female sample. Methods: This mixed-method study makes use of official arrest data for 218 women leaving Delaware prisons in the mid 1990s, to create group-based offending trajectory models. A representative subsample of 118 women was interviewed between 2009 and 2011 and asked to conceptualize the mechanisms that led to their desistance or persistence in offending. Results: Multinomial logistic regression analyses reveal that for some of the sample, age at the time of release from prison has a positive effect on the likelihood that women will belong to a desisting trajectory group rather than the most deviant reference group. Interview narratives demonstrate that in navigating the post-incarceration gendered experiences of securing employment, family reunification, and substance abuse recovery, maturity, clarity about one’s personal responsibility for linked failures, and a desire to transform one’s identity were significant factors that preceded the capacity to excel in those reentry domains. Conclusions: These findings lend support for the applicability of ITD for women’s desistance experiences. As older women appear to express a reentry goal orientation that diverges from that of their younger counterparts, gender-responsive rehabilitation agendas must also include programming that increases the likelihood that participants will connect failures sooner so that the prosocial benefits of a healthy identity change can be enjoyed for longer.