Students at High Achieving Schools (HASs) have recently been identified as an at-risk population, and excessive pressure to excel is considered the cause of this maladjustment. However, the specific aspects of pressure that lead to these outcomes have yet to be comprehensively explored. In two schools, one public and one independent, this study examined multiple constructs potentially implicated: feelings of pressure to succeed from different sources (parents, teachers, coaches, the self, and friends) and total felt pressure. Also considered are dimensions of being overextended across commitments, including hours of sleep, homework, and levels of associated strain and enjoyment. These indices were all examined in relation to adolescents’ internalizing and externalizing symptoms, as well as feelings of disengagement with school, after controlling for attachment to both parents. Results showed that total felt pressure, and pressure felt from the self, were most notably related to internalizing symptoms and disengagement with school. Additionally, strain from commitments showed unique links with depression, anxiety, and negative feelings about school. Finally, enjoyment from different commitments showed robust links with feelings about school. Overall, the different pressure predictors showed sporadic links with externalizing behaviors and substance use. Findings are discussed in terms of directions for interventions as well as future research with HAS populations.