Individuals' expectations are strong predictors of their behaviors; educational expectations predict enrollment in postsecondary education. Yet in many cases, a youth's previous educational expectations are not met or are exceeded. This study examines correlates of educational expectations and unexpected educational attainment using longitudinal data from Monitoring the Future, a U.S. national study. Demographic characteristics, educational experiences in high school, and other risk and protective factors were related to expectations for educational attainment during high school. Logistic regressions indicated that high school curriculum, average grades, educational aspirations, and parents' educational level were particularly strong indicators of youth not meeting their expectation to graduate from a 4-year college, or graduating from college despite expecting not to graduate by age 25/26. We discuss the implications of unexpected pathways in terms of discontinuity during transitions and consider the implications for improved educational and career counseling during high school.