This study draws on the integrated assessments of child welfare caseworkers to reveal how children’s school behavior and academic experiences are intertwined with their family lives and maltreatment experiences. Previous Chapin Hall studies focused on the educational experiences of all children in foster care in a large urban school district. In this study, we focus on the experiences of a subset of children statewide at the point when they become involved with the Illinois Department of Children and Family Services. The nature of the information in the integrated assessments makes it possible to consider the educational status of children in the context of their maltreatment and prior school experiences. Findings suggest that the majority of children in this study who struggled academically were on that trajectory before they were placed in out-of-home care. This report raises issues for discussion concerning the roles of schools and the child welfare system in supporting the educational progress of vulnerable children, before the peak of family crises and after placement in out-of-home care.