Although some research suggests that schools can be a source of protective factors for students, the processes by which school environments impact students' behavior, performance and adjustment over time are not clear. Guided by both self-determination theory and hope theory, this article evaluated reciprocal effects among adolescent perceptions of the school environment, engagement in learning, hope, and academic achievement. Using a sample of 423 students (M age 15.72 years; 46.7% female; 77.6% white; 30.9% eligible for FRPL) from five small secondary schools in the upper Midwest, students' perceptions of the school environment were linked to engagement in learning, which, in turn, was linked to change in academic achievement and hope over the span of 1 year. Evidence was found for reciprocal links between earlier levels of engagement and hope and later perceptions of the environment. These results suggest that the school environment represents a potential leverage point for educational reform, and interventions that target students' perceptions of autonomy, teacher/peer support, and goal orientation may be able to promote engagement, hope, and academic achievement. In addition, such changes may create a positive feedback loop in which change in academic performance and adjustment accelerate over time. (Contains 3 tables and 2 figures.)