Research has identified several student and school characteristics that might be altered to reduce student deviance. Most of this research, however, fails to address whether gender moderates these relationships; that is, most studies do not distinguish between the effect of school-related factors on boys' and girls' delinquency and drug use. In the current study, data from a nationally representative sample of 13,450 students in 253 public, nonalternative, secondary schools are used to examine hierarchical linear models of the relationships between student bonding, communal school organization, and male and female delinquency and drug use. Gender differences in the overall model of relationships are found as are differences in the relationships between student bonding elements and delinquency. Gender differences are 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. Implications for theory and prevention are discussed.