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The last few decades have been marked by greater pressure to attend college and notable increases in the number of adolescents who expect to graduate from college; despite these expectations, however, 40% of undergraduate students do not graduate from post-secondary institutions. Psychological well-being may impact whether students meet their educational expectations. The present study utilized the public-use Add Health data and conducted cross-lagged SEM analyses to examine the predictive power of educational expectations on educational attainment and investigate the impact of depressive symptoms across adolescence and early adulthood on educational attainment. Preliminary results indicate high levels of depressive symptoms may reduce adolescents’ educational attainment, but high educational expectations may buffer against this drop in attainment.