Although the psychological impacts of cyberbullying victimization (CBV) have been documented, research is inconclusive about the role of contextual factors in the association between CBV and student engagement. Sampling 16,237 adolescents from 43 schools in Delaware, we used multilevel modeling to test how CBV was associated with emotional and cognitive-behavioral engagement at both the student and school levels, with the control for demographic factors and traditional bullying victimization (TBV). We also examined the moderating effects of school climate and grade level on the association between CBV and student engagement. CBV had a small but significant positive association with emotional engagement and a small but significant negative association with cognitive-behavioral engagement. School-level climate intensified the negative association between student-level CBV and cognitive-behavioral engagement and mitigated the positive association between student-level school climate and emotional engagement. The positive association between CBV and emotional engagement was stronger for high school than middle school students, whereas the negative association between CBV and cognitive-behavioral engagement was stronger for middle than high school students. The findings support the promotive role of positive school climate in student engagement promotion. The findings also support the healthy context paradox, which suggests that bullying victims' engagement in schools may be exacerbated in a social context with positive school climate perceived by the group members. (PsycINFO Database Record (c) 2020 APA, all rights reserved).