When a woman leaves prison, she enters a world of competing messages and conflicting advice. Staff from prison, friends, family members, workers at halfway houses and treatment programs all have something to say about who she is, who she should be, and what she should do. The Ex-Prisoner’s Dilemma offers an in-depth, firsthand look at how the former prisoner manages messages about returning to the community. Over the course of a year, Andrea Leverentz conducted repeated interviews with forty-nine women as they adjusted to life outside of prison and worked to construct new ideas of themselves as former prisoners and as mothers, daughters, sisters, romantic partners, friends, students, and workers. Listening to these women, along with their family members, friends, and co-workers, Leverentz pieces together the narratives they have created to explain their past records and guide their future behavior. She traces where these narratives came from and how they were shaped by factors such as gender, race, maternal status, age, and experiences in prison, halfway houses, and twelve-step programs—factors that in turn shaped the women’s expectations for themselves, and others’ expectations of them. The women’s stories form a powerful picture of the complex, complicated human experience behind dry statistics and policy statements regarding prisoner reentry into society for women, how the experience is different for men and the influence society plays. With its unique view of how society’s mixed messages play out in ex-prisoners’ lived realities, The Ex-Prisoner’s Dilemma shows the complexity of these women’s experiences within the broad context of the war on drugs and mass incarceration in America. It offers invaluable lessons for helping such women successfully rejoin society.