<p>Drawing upon secondary data from the Australian Longitudinal Study on Male Health (‘Ten to Men’), this study examines the influence of sexual orientation, adherence to traditional masculinity norms, and experiences of traditional bullying and cyberbullying on the severity of depression among adolescent boys. A nationally representative sample of 841 adolescent boys was analyzed using path analysis to assess the relationships between sexual orientation, conformity to traditional masculinity, bullying perpetration, bullying victimization, and depression severity. The secondary data analysis revealed significant associations between traditional bullying perpetration, traditional bullying and cyberbullying victimization, and depression severity. Furthermore, conformity to traditional masculinity was found to directly and indirectly predict depression severity, mediated by traditional bullying perpetration. Bisexual and questioning youth exhibited higher levels of depressive symptoms regardless of bullying experiences, while gay youth were more likely to experience cyberbullying victimization. Findings from this study underscore the nuanced interplay between sexual orientation, adherence to traditional masculinity norms, bullying experiences, and depression severity among adolescent boys. It emphasizes the need for tailored interventions to address the mental health challenges faced by diverse youth populations. Policy efforts should prioritise the development and implementation of comprehensive strategies to combat bullying, both in traditional and cyber settings, particularly among vulnerable populations such as bisexual, questioning, and gay youth. Additionally, interventions aimed at challenging rigid notions of masculinity and promoting inclusive environments are essential to fostering mental wellbeing among adolescent boys.</p>