Traditionally, face-to-face bullying has been major problem among adolescents, especially those deemed at-risk. With the rise in the use of and advancements in mobile technologies, the Internet 2.0, and smart phones, a new form of bullying has been on the rise resulting from the increase in access to technologies and by association, social media outlets such as Facebook, Instagram, and Twitter. Cyberbullying, as it has been denoted, can occur at any time of the day on all social media platforms resulting in the potential of face-to-face victims enduring the abuse of their aggressors on an almost 24/7 basis. As such, cyberbullying can trigger numerous emotional and physical stressors among students. The purpose of this study was to discover the perceptions middle school students have about cyberbullying and their role as either victim, perpetrator, or bystander. The results of the study speak to a broader and emerging narrative indicating the psychological challenges faced by developing adolescent minds in negotiating face-to-face and virtual relationships.