The objective of this study was to examine the role of school connectedness in the association between a history of family involvement with child protective services (CPS) and symptoms of psychological distress and delinquency among youth. Data were obtained from 3181 participants within the 2009 cycle of the Ontario Student Drug Use and Health Survey, a province-wide school-based survey of 7th–12th grade students. The survey employed a two-stage cluster design and analyses presented include adjustments for this complex sample design. Results indicated that the association between CPS involvement and psychological distress varied with school connectedness. CPS involvement was more strongly associated with psychological distress among students with low-school connectedness than students with high-school connectedness. School connectedness did not signifi cantly moderate the link between involvement with CPS and delinquency. Results suggest that improving school connectedness may be one way to protect youth with a history of family involvement with CPS and, along with effective mental health services, reduce the accumulation of risks as youth transition into adulthood.