The aim of this study was to determine the organizational characteristics and behaviors that contribute to sustaining a culture of academic optimism as a mechanism of student achievement. While there is a developing research base identifying both the individual elements of academic optimism as well as the academic optimism construct itself as contributors to student achievement, little information exists to assist school leaders in identifying specific organizational practices that sustain collective teacher efficacy, academic emphasis, and trust in students and families. This study employs case study methodology to investigate faculties\u27 interpretations of academic optimism by examining the organizational and instructional practices at three well performing Virginia high schools. Gathered data includes information obtained through direct interviews with 18 (six at each site) faculty members, observations from 12 (four at each site) classrooms, and a review of each school\u27s vision or mission statements, improvement initiatives, and course offerings and enrollments