Observational methods are increasingly used to assess the impact of school-based interventions. Yet, few studies have used observations in nonclassroom settings, such as hallways or the cafeteria, or explored aspects of the school context that may be related to the observed behavior. The current study used a multilevel approach to examine associations between observed rule violations and contextual predictors, including characteristics of observations (e.g., location and number of students present) and schools (e.g., perceived management, discipline referrals). Analyses were conducted on data from 37 elementary schools. Within schools, rates of physical and verbal violations varied by location and significantly higher rates of rule violations were observed in areas with high student density. Between schools, only a negative association for observed verbal violations and staff perceptions of the status of nonclassroom management systems was significant. The significance and relevance of these findings for both educators and applied researchers are discussed.