Results show significant associations between emotionality, bullying, and perceptions of family and school environments, with particular differences emerging between boys and girls. The findings indicated that internalizing and externalizing difficulties, along with many of the context-related factors (academic performance) and student assessments of contextual moderator variables (family functioning and school environment and climate factors), were associated with students' engagement in and experience of bullying and victimization by their peers. The extent to which maladaptive peer relations were associated with individual emotional and behavioral difficulties appears to be influenced by the environmental factors that adolescents reportedly experience. However, these associations varied by gender, in that, different patterns of factors were associated with the likelihood of girls being a bully or victim versus boys. Data were collected from 1,474 students from suburban or rural regions; teachers provided completed behavior rating scales on each student in the sample. Tables, figures, notes, and references