Objective: 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. Methods: Data were gathered from 3181 participants within the 2009 cycle of the Ontario Student Drug Use and Health Survey, a province-wide school-based survey of 7th to 12th grade students. The survey employed a two-stage cluster design, and the analyses reported include adjustments for this complex sample design. Results: Analyses 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 significantly moderate the link between involvement with CPS and delinquency. Conclusions and Implications: Results suggest that fostering 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.