This study examined the relationships between enabling structures, academic optimism, and student achievement to determine whether academic optimism served as a mediator between the two. Student achievement was measured using both criterion-referenced and norm-referenced tests. Findings indicated a relationship between academic optimism, enabling structures, and student achievement. Also, academic optimism appeared to serve as a mediator between enabling structures and norm-referenced assessments but did not correlate with criterion-referenced tests. This study is one of only a few seeking to establish connections among enabling structures, academic optimism, and student achievement, measured at the school level, in elementary schools. The use of mediation also offers a unique perspective on the literature.