AbstractDespite existing research on the factors associated with problematic social media use (PSMU), cyberbullying (CB), and cybervictimization (CV) among youth, few studies have explored the relationships between these variables. Rooted in the Maladaptive Coping Theory, this study investigates the complex dynamics of digital behaviors among Italian preadolescents, exploring the interplay between PSMU, moral disengagement, retaliation, and their connections with cyberbullying and cybervictimization. A total of 489 participants (Mage = 11.90, SD = 0.783; 50.3% female) from schools in southern Italy completed an online self-report questionnaire. Descriptive analyses were conducted and correlations between variables were computed. Mediation and moderation analyses were performed using PROCESS in SPSS 27.0. The results of the study indicated that PSMU positively predicted both CB and CV. Moral disengagement (MD) was identified as a mediator in this association, elucidating the role of justifications and cognitive restructuring in facilitating negative online behaviors. Most notably, retaliation emerged as a moderator that amplified the effects of PSMU on cyberbullying and cybervictimization. These findings underscore the pivotal role of PSMU in shaping digital landscapes for preadolescents and highlight the need for tailored interventions. In addition, they highlight MD as a maladaptive coping strategy in the online realm, revealing its instrumental role in perpetuating negative online behaviors. This study’s insights suggest the need for interventions to address the complexity of young people’s online interactions and promote a safer digital environment.