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Bystanders play an important role in either facilitating or inhibiting bullying. However, knowledge is still lacking regarding factors that contribute to positive bystander behaviors. Therefore, this study aimed to investigate the associations between school connectedness and willingness to intervene within the context of anti-bullying climate, using a three-year longitudinal design among a group of adolescents (N = 4,718). The findings showed that both contextual factors were positively related to students’ willingness to intervene in bullying at the between-person level; in addition, school connectedness was related to willingness to intervene bidirectionally at the within-person level. Overall, this study highlights the role of contextual factors in empowering bystanders and promoting positive bystander behaviors, which provides guidance for bullying prevention and intervention.