Cyberbullying has become a pervasive issue, often linked to Dark Triad personality traits—Machiavellianism, Narcissism, and Psychopathy. However, less attention has been given to the role of antagonistic social emotions, particularly Schadenfreude (pleasure in others’ misfortune) and Glückschmerz (pain at others’ success), in driving cyberbullying behaviors. This study examines the interplay between these emotions and Dark Triad traits to uncover the psychological mechanisms behind cyberbullying. Using a fuzzy-set Qualitative Comparative Analysis (fsQCA), this study identifies three equifinal configurations that contribute to cyberbullying. The findings suggest that interventions should target the emotional rewards associated with cyberbullying rather than solely focusing on personality traits. From a theoretical perspective, this study provides a novel perspective on cyberbullying by integrating emotional and personality-based explanations using a configurational approach. The use of fsQCA allows for a more comprehensive understanding of the multiple pathways leading to cyberbullying, highlighting the need for multi-faceted intervention strategies. Digital platforms, educators, and policymakers can develop strategies to mitigate Schadenfreude- and Glückschmerz-driven cyberbullying by promoting emotional regulation, empathy training, and stricter content moderation policies.