Online harassment, particularly cyberbullying and the non-consensual sharing of intimate images, is a widespread phenomenon among adolescents and young adults. Descriptive research was carried out to investigate any differences among Italian school classes in the perception of cybercrime through a real-case scenario. Following the Italian school system, the final sample of 1777 adolescents (Mage = 15.37, SD = 1.65; Male = 52%) was divided into three groups based on the school class attended: middle school (N = 562; Mage = 13.37, SD = 0.48); high school biennium (N = 728; Mage = 15.55, SD = 0.50), and triennium (N = 487, Mage = 17.40, SD = 0.71). Participants completed a self-report questionnaire investigating the use of the Internet and the perception of a real case scenario involving the non-consensual sharing of intimate images and cyberbullying received by the National Centre for Combating Child Pornography Online (NCPO). Results showed differences among the three groups’ perceptions of the event’s features, motivations underlying the offense, victim-blaming and harassment justification (e.g., cyberbullying, in particular non-consensual sharing of intimate images, is recognized as a crime as age increases). The findings provide significant insights for future research and age-specific factors to consider when developing prevention programs for online risks.