This study examines whether disconnection between educational aspirations and expectations is associated with socioeconomic status, academic performance, academic risk-related behaviors and related psychosocial factors in an ethnically and economically diverse sample of early adolescents from a public middle school (N = 761). Results suggest that students who aspire to achieve more than they expect to achieve also are likely to have more economically disadvantaged backgrounds and poorer academic performance. These students also show a variety of academic and social risks. Specifically, students whose aspirations exceeded their expectations reported lower levels of school bonding, higher levels of test/performance anxiety, and elevated behavioral/emotional difficulties. Results are discussed in terms of social-cognitive theory as well as applications for promoting student social and academic success. (Contains 4 tables.)