Family has long been central to our understandings of offending and desistance. However, in research on adult offenders or prisoners, the focus is more often on romantic partners, children, and peers than on families of origin. This article underscores the continuing importance of families of origin in the reentry and desistance processes of urban female African American former prisoners and probationers. The author demonstrates that these relationships play an important part in women’s identities, even when they often come into direct conflict with desistance efforts. Thus, these women must learn to balance sometimes-contradictory messages of their obligations within their family and their emerging identities as desisting former offenders.