Despite the dramatic increase in incarcerated mothers that has occurred in the past decades, there is a paucity of family research focusing on the children affected by maternal imprisonment. The present study investigated family environments and intellectual outcomes in 60 children between the ages of 2 and 7 years during their mothers’ incarceration. Multiple methods were used to collect data from children, mothers, and children's nonmaternal caregivers. Results indicated that most children experienced multiple risks across contextual levels. Cumulative caregiver sociodemographic risks predicted children's cognitive abilities, although quality of the home and family environment mediated this relation. Results underscore the importance of children's family environments and highlight the need for increased monitoring, service delivery, and longitudinal research with children of incarcerated mothers and their families.