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There is continued and growing concern regarding adolescent mental health, especially as it may relate to interpersonal peer interactions and relationships in the school environment. Scholars across multiple disciplines, as well as public health and school officials, continue to seek understanding regarding perceptions of the school environment, student emotional well-being, and bullying behavior. Within criminology, Agnew’s macro-level general strain theory has been posited to explain the processes through which the school environment/climate may influence such factors. In this paper, we analyze predictions from this theory utilizing data from 7,867 students nested within 314 schools across the United States. In doing so, we attempt to disentangle the hierarchical sources of variation in the associations between strain, negative affect, and bullying behavior. Preliminary findings suggest general support for posited theoretical relationships, though the strength of support varies depending on modeling strategy. Considering the importance of the decomposition of such effects, suggestions for theoretical and model specifications for multi-level phenomena are provided.