This research addresses behavior difficulties and maladaptive coping among African American children and adolescents, and the manner in which these outcomes differ among those with incarcerated mothers. The study also provides an in-depth analysis of the experiences of mothers during and after their incarceration. Earlier investigations suggested that mothers’ victimization and offending, including drug use, are related to children’s emotional and behavioral outcomes. Hence, this research extends an ongoing project by investigating the nature of this relationship using aggregate data on adolescent health outcomes. Generally, most research addresses parental incarceration, typically followed by negative responses of male youth. Less research has evaluated the outcomes of parents’ incarceration on African American children and adolescents specifically. This is particularly true among those with incarcerated mothers. Additionally, examinations have highlighted the role of fathers’ incarceration on negative family functioning, yet we know less about the impact of mothers’ imprisonment and re-entry on children’s behavior. Many of these mothers are single and live in poverty, and their economic situations lead to higher risks of recidivism, deleteriously affecting their children. Moreover, several of them are raising children while experiencing traumatic mental health concerns amid drug usage with minimal support or treatment. For the current project, special attention is also placed on the mothers’ experiences with contact with children, prior history of substance abuse, mental illness, treatment for drug and alcohol problems, and coping with separation from children in an attempt to reveal the subsequent, harmful impact on children’s behavioral adjustment.