The present study used a unique measure of self-perceived gender typicality to better examine the association of gender with cyber victimization and perpetration. Participants were 297 adolescent males and females recruited from independent schools in grade 8 (M[subscript age] = 13.8) and grade 10 (M[subscript age] = 15.8) who completed a self-report survey. Multiple regression analyses revealed that only for males, high other-gender typicality and low same-gender typicality were associated with high cyber victimization, but when same-gender typicality was high there was no association. Independent associations of same- and other-gender typicality with cyber perpetration were present only for males. Findings highlight that the importance of considering same- and other-gender typicality for adolescent boys' engagement in cyberbullying.