This paper advances conceptualization of maternal distress following incarceration. We utilized a multiple case study methodology based on interviews with 10 mothers who demonstrated various permutations of "the triple threat" (depression, domestic violence, and substance abuse; Arditti & Few, 2006). Findings suggest that depressive symptomology persisted and worsened for mothers in our study and that maternal distress was indicative not only of women's psychological state, but also a relational and situational construct that embodied women's core experience. Maternal distress was largely characterized by health challenges, dysfunctional intimate relationships, loss related trauma, guilt and worry over children, and economic inadequacy. Further, maternal distress seemed to be intensified by the punitive traumatic context of prison and lessened by rehabilitation opportunities as well as support by kin and probation officers after reentry. Recommendations for clinicians and professionals who work with reentry mothers center around the need to alleviate maternal distress and better address women's emotional and physical health needs during incarceration and reentry.