Despite the critical role educators play in the lives of students, little research has been conducted on their perceptions of digital media, bullying behaviors and prevention, and the development of disciplinary policy. As educators are tasked with monitoring student behaviors both inside and outside the classroom, how they conceptualize student behavior emerges as a site for possible mediations in the culture of bullying that permeates 21st century schooling. The purpose of this study was to examine how teachers understand digital life, how they represent themselves within the culture of social media, and the effects those perceptions have on the enforcement of or dismantling of bullying as a social institution. The results of this study show that educators are less adept at negotiating digital life and are largely unaware of the impactful nature of online relationships. While bullying has distinct social drawbacks including the maintenance of a horizontally hostile culture, the social benefits of bullying are proposed as emergent sites of intervention. As educators are ever more faced with issues of disciplinary conduct, they have developed a chosen ignorance to justify their lack of knowledge about online and offline bullying cultures. The perception that bullying is an insurmountable issue is a common perception among educators in this sample however this research suggests that through recognizing the function of bullying educators and administrators alike can develop deterrent policies that work outside the abstinence-based models for bullying prevention and recuperative-based models for soothing victims.