This study uses quantitative and qualitative analysis of interviews of 40 ex-offenders to examine the differences between women and men in motivations to desist from drugs and crime and expectations and experiences of criminal record expungement. Both men and women seek opportunities for personal gain through desistance and record clearance, but women are more likely to be motivated by moral and religious influences and concern about their reputation. Caregiving is especially important to women as a personal obligation and a professional aspiration. During efforts to desist and to move forward with a law-abiding lifestyle, women are more likely to express desires to break from the past and replace their criminal identities, but they also experience greater difficulty than men do in their efforts to change their living environment and associates. These findings emphasize the importance of both individual decision-making and gendered social roles and contexts in the reentry process.