Teachers serve as the natural raters of students within the school and classroom contexts. Yet teachers' ratings of their students may vary based on these contextual factors. The current study explored the extent to which teacher perceptions of the school environment predict their longitudinal ratings of student behaviors. Data for this study come from 702 teachers in 42 elementary schools. Teachers self-reported their perceptions of the school context at a single time point, and provided ratings of their students' behavior via the Teacher Observation of Classroom Adaption-Checklist (TOCA-C) across three school years. Latent profile analysis identified three latent classes of teachers based on their ratings of school organizational health, burnout, and efficacy. A regression framework demonstrated an association between the baseline profiles in relation to TOCA-C ratings of student behavior across 3 years. Teachers with more favorable perceptions of the environment had lower initial ratings of concentration problems, disruptive behavior, and internalizing symptoms, and higher ratings of prosocial behaviors and family involvement. They also showed slower growth in their ratings of emotion dysregulation and greater increases of their ratings of family involvement over time. This work is particularly important for determining the extent to which teacher ratings may be biased by teacher and contextual factors, and may have implications for the identification of teachers who may rate students poorly over time.