This study adopts a social-ecological/contextual perspective to explore Arab youth involvement in cyberbullying perpetration. We explored the association between individual (age, gender, and impulsivity), family (socioeconomic status and parental monitoring), and community (experiencing neighborhood violence) characteristics and cyberbullying perpetration. A moderation model exploring individual, family, and context interactions was tested. A sample of 3,178 Arab students in Grades 7 to 11 completed a structured, anonymous self-report questionnaire. The findings suggest that almost 14% of the participants have cyberbullied others during the last month. Adolescent boys with high impulsivity, low parental monitoring, and who experience a high level of violence in their neighborhood are at especially high risk of cyberbullying perpetration. Parental monitoring moderated the effects of impulsivity and experiencing neighborhood violence on adolescents’ involvement in perpetrating cyberbullying. Furthermore, the results show that impulsive adolescents who experience high levels of neighborhood violence are at higher risk of cyberbullying perpetration than low impulsive children who experience the same levels of neighborhood violence. The results highlight the central role parenting plays in protecting their children from involvement in cyberbullying perpetration by buffering the effects of personal and situational risk factors.