The authors draw on developmental psychopathology, life course sociology, and scholarship on educational processes to develop a conceptual framework for understanding the association of children's mental health problems with educational attainment. They use this framework to address two empirical gaps in prior research: lack of attention to mental health trajectories and the failure to consider diverse explanations. Using data from the Children of the National Longitudinal Surveys of Youth data set, the authors identify latent classes that characterize trajectories of internalizing and externalizing problems from childhood through adolescence. Youths in the classes vary significantly in their likelihoods of high school completion and college entry. The authors evaluate the ability of three sets of mediators to explain these patterns: academic aptitude, disruptive behaviors, and educational expectations. Educational expectations are important mediators independent of academic aptitude and disruptive behaviors. Social responses to youths' mental health problems contribute importantly to their disrupted educational trajectories.