<p>Gaining and maintaining popularity is a central concern during early adolescence, and adolescents experiencing social status insecurity may turn to bullying in attempts to improve their standing. However, it remains unclear whether bullying truly yields its intended social rewards and whether these associations differ across classroom popularity norms. This study investigated bullying as a potential mediator linking social status insecurity to popularity over time and examined classroom popularity norms as a contextual moderator. A total of 2,310 adolescents (51.6% boys at T1; <i>M</i>_age = 12.36, <i>SD</i> = 0.69) from 49 classes were assessed across five waves over two years. Random-intercept cross-lagged panel models showed that bullying did not mediate the association between social status insecurity and popularity, regardless of peer-nominated or self-reported measures. Multi-group analyses further indicated that popularity norms moderated within-person associations differently: in low-norm classrooms, associations were generally non-significant, whereas in high-norm classrooms, social status insecurity and bullying were positively associated, yet bullying did not increase subsequent peer-nominated popularity and even negatively predicted self-reported popularity. These findings highlight that bullying rarely produces the expected social benefits, providing insights for more targeted and effective interventions to reduce bullying.</p>