Many high school students who want to attend college never actually enroll. Multiple factors like barriers (e.g., financial, discrimination) and poor academic achievement prevent some high school students from matriculating to college. Researchers must form a nuanced understanding of multidimensional factors that predict college enrollment. The purpose of this dissertation is to investigate the extent to which psychosocial academic behavioral skills (PABS) predict college enrollment in two and four year colleges. A cross-sectional, survey-based methodology was used to address the research questions. Data from operational research by ACT, Inc. using the Engage 10-12 instrument were used to analyze students’ psychosocial academic behavioral skills. Standardized test scores and high school GPA were used to measure academic achievement. College enrollment data were gathered from the National Student Clearinghouse. A large, diverse sample of over 4,100 high school students in 10th, 11th, and 12th grade was analyzed using logistic regression and hierarchical generalized linear models. Select psychosocial academic behavioral skills demonstrated positive relationships with four-year enrollment. Relationships between PABS and two-year college enrollment were smaller than the observed relationships between PABS and four-year college enrollment. Bootstrapping was used to determine if psychosocial academic behaviors predicted college enrollment or if this effect was mediated via academic achievement. Moderation and partial mediation effects were observed. By understanding student characteristics related to college enrollment, researchers and policymakers are better equipped to help young people matriculate to postsecondary institutions.