Research shows that prior academic achievement is a strong predictor of future academic performance. For some students, the transition from one educational environment to another is associated with academic challenges and achievement loss. This study examined the extent to which achievement loss during the transition from middle school to high school later impacted college outcomes. Using data from the National Educational Longitudinal Study 1988/2000 (NELS: 88/2000), the results from a logistic regression analysis suggest that high-achieving middle school students who experienced achievement loss were more likely to leave their first college than high-achieving students who did not experience achievement loss. (Contains 3 tables.)