Children in out-of-home placements are at increased risk for a multitude of poor educational outcomes. The federal Fostering Connections to Success and Increasing Adoptions Act of 2008 requires child welfare and education systems to collaborate towards improved educational outcomes for children in foster care. This study performed focus groups with ground-level stakeholders from child welfare and education systems to solicit information on the barriers, strategies, and daily experiences of working across systems towards educational success for children in child welfare in a large, urban area. Ten focus groups were completed with a total of 90 study participants. Knowledge and implementation of policies related to the educational needs of children in foster care was highly variable among participants. Across all groups, ineffective and limited cross-system communication, role uncertainty among stakeholders, and prevalence and complexity of behavioral health needs among children were identified as barriers to achieving educational success for children in foster care. Innovative approaches to cross-system collaboration between education and child welfare systems are needed to affect these positive outcomes. The complexity of mental health service provision for children in foster care with behavioral problems will require improved cross-system collaboration.