This article presents an emergent conceptual model of the features and links between cumulative disadvantage, maternal distress, and parenting practices in low-income families in which parental incarceration has occurred. The model emerged from the integration of extant conceptual and empirical research with grounded theory analysis of longitudinal ethnographic data from Welfare, Children, and Families: A Three-City Study. Fourteen exemplar family cases were used in the analysis. Results indicated that mothers in these families experienced life in the context of cumulative disadvantage, reporting a cascade of difficulties characterized by neighborhood worries, provider concerns, bureaucratic difficulties, violent intimate relationships, and the inability to meet children's needs. Mothers, however, also had an intense desire to protect their children, and to make up for past mistakes. Although, in response to high levels of maternal distress and disadvantage, most mothers exhibited harsh discipline of their children, some mothers transformed their distress by advocating for their children under difficult circumstances. Women's use of harsh discipline and advocacy was not necessarily an "either/or" phenomenon as half of the mothers included in our analysis exhibited both harsh discipline and care/advocacy behaviors. Maternal distress characterized by substance use, while connected to harsh disciplinary behavior, did not preclude mothers engaging in positive parenting behaviors.