This chapter explores the extent to which parents are aware of the risk their children being exposed to cyberbullying and the extent to which they have the competencies to tackle the problem. Relying on Bronfenbrenner’s theory of human development we position our analysis within a bioecological model which recognises that the issue of cyberbullying is complex and multi-systemic. We undertook a parent focused evaluation of 908 parents’ experiences of the internet. The aim was to analyze parental online facility, perceived confidence, and interactions with their children in regards to internet use and cyberbullying specifically, to see what might be gleaned about how parents approach cyberbullying and on-line safety, and how that might inform future practice in helping to better guide and educate parents. The results of the study revealed that parents tended to use different social media and apps to those used by their children which left them unfamiliar with the specific dangers their children were exposed to and they were also found to over rely on their children self-reporting about their safety on-line. The study revealed that parents use the internet as much as their children but not the same social media and that there was a need for them to engage in a more meaningful way with their children in relation to the risk of cyberbullying.