Background: The study of adolescents’ behaviours and attitudes is crucial to define interventions for the containment of deviance and social discomfort. New ways of social interaction are crystallising violent behaviours which are moving more than ever on a virtual sphere. Bullying and cyberbullying share a common behavioural matrix that has been outlined through specific environmental and individual characteristics. Methods: A survey carried out in Italy in 2019 on a statistical sample of 3273 students highlighted the influence of several social and individual variables on deviant phenomena. Risk and protective factors in relation to the probability of involvement in bullying and cyberbullying have been shown through a bivariate analysis and a binary logistic regression model. Results: The study shows that presence of stereotypes and social prejudices, tolerance to violence and high levels of self-esteem have resulted as the main risk factors. On the other hand, low levels of tolerance related to the consumption of alcohol and drugs, high levels of trust towards family and friends and being female have been identified as protective factors. Conclusions: This research confirms the validity of several theories on bullying and cyberbullying phenomena. Furthermore, it identifies specific risk and protective factors and their influence on deviant behaviours, with a focus on environmental characteristics which appear as the key field of work to enhance adolescents’ well-being.