Gender differences in the overall model of relationships were found as were differences in the relationships between student bonding elements and delinquency. However, gender differences were not found in the relationships between student bonding elements and drug use, nor in the relationships between communal school organization elements and delinquency and drug use. Study limitations and future research were outlined and discussed. Most existing research has failed to address whether gender moderates the relationships between student deviance and the school-related factors of student bonding and communal school organization. This study seeks to address these gaps in research. Using a nationally representative sample of 13,450 students from 253 schools, hierarchical linear models were run to examine the potential gender differences in the relationship among school-level communal school organization, individual-level student bonding, and individual-level student deviance (male and female delinquency and drug use). Tables, references, and appendix