Excessive use of exclusionary school discipline with Black students is a persistent, systemic problem in U.S. schools with potential to affect students' perceptions of their school. For example, students may notice racial differences in out-of-school suspensions, which may relate to how academically engaged they feel and the extent to which they view the school's disciplinary environment as positive. The current study investigated school-level racial discipline disproportionality and observed classroom-level, positive behavior supports in relation to student perceptions of academic engagement and school disciplinary environment by fitting a series of three-level models, which included data on students (N = 17,115), classrooms (J = 310), and schools (K = 53). Two metrics of discipline disproportionality were used (i.e., the risk ratio and the risk difference) and moderation was examined through cross-level interactions. Results indicated that, regardless of race, students perceived the disciplinary environment as significantly less favorable in schools with greater racial discipline disproportionality when measured by the risk ratio, but not when measured by the risk difference. Using different disproportionality metrics in education research has important implications for policies and practices to identify and address the issue. How discipline disparities relate to the way that students perceive the disciplinary environment will likely inform intervention efforts for school psychologists. [This article is published in "Journal of School Psychology" (2019).]