In this thesis, I investigate the relationship between cultural capital and school engagement. Cultural capital has been investigated in its relation to academic achievement and attainment, with the ultimate finding that it has little direct causal effect on student success. A lack of school engagement has been determined to be a significant contributor to high school dropout. While cultural capital researchers have found differences in classroom behaviors related to levels of cultural capital and socioeconomic background, few have examined these differences in relation to attachment or engagement with schooling. In addition, while some researchers have begun to examine engagement as an educational outcome, none have examined whether culture may influence engagement. To this end, I investigate the relationship between cultural capital and school engagement, as well as the associations among cultural capital, engagement, and high school dropout. I find that, as predicted, cultural capital is significantly associated with school engagement. I also find that cultural capital is significantly associated with high school completion, with and without controlling for engagement. Consistent with previous work, lower engagement is significantly associated with high school dropout. I also run several analyses to investigate these relationships, with findings pointing toward the importance of cultural capital during early development, reading, and student excitement in school as key predictors of continued schooling success (or failure). I conclude with a discussion of limitations of the current study and promising avenues for further investigation.