This study describes how parental involvement not only is shaped by the school context but also shapes the school context for college opportunity. The study also describes the ways other aspects of context, particularly the higher education context and the state and economic context, shape parental involvement. Although parental encouragement and involvement appear to be important facilitators of college enrollment, this study describes the barriers that limit parental involvement not only for low-socioeconomic status parents but also for middle-SES parents. The study relies on data from descriptive case studies of 15 high schools, three in each of five states: California, Florida, Georgia, Maryland, and Pennsylvania. The five states were chosen based on their variation in economic, political, demographic, and educational characteristics. The authors developed data collection protocols based on the conceptual framework and a literature review of the predictors of college enrollment. Using the conceptual model as a guide, three themes emerge from the data: (a) parents shape college opportunity for their children, but involvement varies based on socioeconomic status; (b) parental involvement is shaped by, and also shapes, the school context for college opportunity; and (c) parental involvement is also shaped by the higher education context and the social, economic, and policy context. The findings from this study improve the understanding of the ways that parental involvement shape college enrollment for different families at different schools in different states. The findings suggest several implications for improving parental involvement.