Information and communication technologies (ICT) play an important role in the social lives of adolescents, as many of the social interactions that once occurred in face-to-face contexts are now occurring through digital technologies. Although many of these interactions are prosocial in nature, adolescents may also engage in high levels of aggression in ICT-mediated contexts (Bauman, 2013; Bauman & Newman, 2013). Furthermore, they often engage in self-monitoring when communicating with peers through ICTs in order to maintain a positive public image (Subrahmanyam, Garcia, Harsono, Li, & Lipana, 2009). These digital behaviors may have implications for how individuals establish and maintain their place within social hierarchies in natural peer contexts (e.g., schools). Drawing on both The Hyperpersonal Theory of Computer-Mediated Communication and Resource Control Theory, the current study examined concurrent associations between digital self-monitoring, cyberaggression, cyber-prosocial behaviors, and popularity. A sample of 273 (112 boys; 161 girls) adolescents attending high schools in the Upper-Midwest of the United States provided data for this study during the fall of the 2014 – 2015 school year. Students completed a series of questionnaires consisting of peer-reports and self-reports of aggressive and prosocial behaviors in face-to-face and digital contexts, peer-reports of popularity, and self-reports of self-monitoring in digital and face-to-face environments. Small positive correlations were found when examining associations between peer- and self-rated cyberaggression and peer- and self-rated cyber-prosocial behavior (rs between .11 and .22). Controlling for face-to-face overt and relational aggression, cyberaggression was negatively related to adolescents’ popularity, particularly for individuals who engaged in low to moderate levels of digital self-monitoring. Cyber-prosocial behavior was positively associated with popularity generally, and specifically for adolescents low in face-to-face prosocial behaviors. Cyberaggression, cyber-prosocial behaviors, and sex also interacted to predict popularity. Analyses revealed that for boys high in cyber-prosocial behaviors, cyberaggression was positively associated with popularity, while the relation between cyberaggression and popularity was not significant for girls or for boys low in cyber-prosocial behavior. Results are discussed within the context of Resource Control Theory and how they may be applied to researchers’ understanding of peer relationships in digital and face-to-face social contexts.