This paper examines cyberbullying as a distinct form of digitally mediated harm that challenges traditional categories of criminal law. Using a comparative doctrinal and case-law analysis of the Omani, American, British, and French legal systems, it evaluates whether existing penal and cybercrime frameworks can genuinely accommodate the specific features of cyberbullying and provide effective protection for victims. The study argues that cyberbullying is defined by a particular constellation of characteristics—deliberate targeting, repetition or persistence, technological amplification, and structural power asymmetry—that qualitatively distinguish it from related offences such as defamation, threats, privacy violations, and unlawful access to information systems. Drawing on key decisions of the United States Supreme Court on online threats and harassment, as well as leading judgments of the European Court of Human Rights and recent rulings of the Omani Supreme Court on insult and violations of private and family life committed via digital means, the paper shows both the flexibility and the limits of applying existing offences to sustained online abuse under robust free-speech guarantees. The comparative findings reveal a fragmented regulatory landscape. French law has moved towards explicit criminalisation of cyberbullying, many U.S. states have adopted specialised anti-bullying statutes within tight constitutional constraints, and the United Kingdom relies on a dispersed set of communications and harassment offences. By contrast, Omani law still addresses cyberbullying only indirectly through general penal and cybercrime provisions, leaving significant gaps regarding behaviours such as impersonation, systematic exclusion, and coordinated digital attacks. In light of these results, the paper proposes a tailored legislative framework for Oman that recognises cyberbullying as an autonomous criminal offence and complements criminal sanctions with preventive, educational, and technical measures, seeking to reconcile robust protection of psychological integrity and human dignity with constitutional guarantees of freedom of expression.