Today's world is no doubt one that continues to be shaped and influenced by the rise of social media platforms. These platforms have spread throughout the lives of contemporary students and, unfortunately, have heightened the severity and prevalence of cyberbullying. The purpose of this paper is to explore the intersections between social studies, social media, character education, and cyberbullying in the middle school setting. We provide middle school social studies teachers with a rationale for understanding why cyberbullying is a critical issue necessary to explicitly address in the social studies classroom by connecting it to both character development and citizenship goals. Additionally, we provide practical applications and resources for social studies teachers to utilize in order to promote critical thinking about and positive interactions with social media in the classroom to address issues of cyberbullying.