Parental involvement in school is an undoubtedly important element of a student’s educational experience and outcomes. Students with elevated emotional and behavioral risks (EBR) tend to experience poor educational outcomes, and research suggests varying levels of parental involvement across domains for these at-risk students. However, there is minimal research on the links between elevated EBR, parental involvement, and academic achievement for high school students. The purpose of this study was to examine the degree to which (a) parental involvement differed between high school students with elevated EBR and students without EBR, (b) parental involvement was related to academic outcomes, and (c) the gap in academic achievement between students with elevated EBR and students without EBR could be attributed to differences in parental involvement. To address these questions, we fit a structural equation model using data from the High School Longitudinal Survey of 2009. The results demonstrated that (a) parental involvement was significantly lower in multiple domains for students with elevated EBR, (b) was significantly associated with academic outcomes, and (c) differences in parental involvement could account for a significant proportion of the achievement gap. Research limitations, directions for future research directions, and implications are discussed.