A growing body of evidence links demographic characteristics such as socio-economic status with exposure to stressful circumstances and physical and mental health outcomes (Adler, Boyce, Chesney, Cohen, Folkman, Kahn & Syme, 1994; Aldwin, 2007; Cohen, Doyle & Baum, 2006). This study applies a stress and coping framework to the relationship between stressful life experience and secondary and post-secondary schooling outcomes among students. This research investigates how parental level of education relates to exposure to stressful circumstances (life events, school stressors, and role strain) and whether these relationships influence four educational outcomes: high school math and reading achievement, college matriculation, and college degree attainment. This study is a secondary analysis of the National Education Longitudinal Study (NELS:88/2000), using a subsample of 7,989 high school students followed between 1988 and 2000. Results showed that students without college-educated parents are exposed to more stressful circumstances. This difference in exposure did not account for group differences in learning outcomes. Still, overall, exposure to certain stressors affects student high school achievement over the entire sample, and total life event stress exposure in high school relates to students' overall ability to finish a college degree. The unique contribution of this work is that it 1) employs a stress and coping conceptual framework applied to high school achievement and post-secondary opportunity; and 2) constitutes a rigorous study with robust statistical controls. This research informs interventions aimed at improved achievement and opportunity among high school students with high stressor exposure, in which low income and students of color are disproportionately represented (Organista, 2007).