Educational attainment is associated with a plethora of positive economic and social implications for individuals, institutions, and the broader society. One factor that has been identified as an important predictor of students’ educational attainment is their educational expectations. Thus, understanding how educational expectations are shaped is important to comprehending how success can be fostered among students from diverse racial backgrounds. This quantitative study was aimed at understanding the process by which students from various racial backgrounds cultivate and reformulate their educational expectations during the high school years. Three research questions were explored in this study: (1) How do various academic and interpersonal factors directly affect students’ educational expectations? (2) How do academic and interpersonal factors indirectly affect students’ educational expectations via their self-perceptions? and (3) How do those effects vary across different racial groups? Using a pretest-posttest design and structural equation modeling techniques, we created a structural model and examined how academic and interpersonal factors directly and indirectly, via self-efficacy and locus of control, influence students’ educational expectations. Particular attention is given to how those effects vary across racial subpopulations. Relationships between the results of this inquiry and earlier studies are complex, with some of our findings confirming and some contradicting those of other researchers. The results of this analysis indicate that the process by which students formulate and reformulate their educational expectations during the high school years varies across racial groups. Recommendations for future research involve considering racial, gender, socioeconomic, and other differences in examining students’ educational expectations and outcomes. We also recommend that future research focus on understanding the reasons why such racial differences exist.