This research study focuses on Maltese secondary school students’ experiences with cyberbullying through the perspectives of educators, experts and high-level policymakers. The literature review delves into the concept of ‘onlife’, highlighting the blurred boundaries between physical and digital spaces and the impact of technology on empathy and relationships. It explores Suler’s theory of the online disinhibition effect, suggesting that the lack of face-to-face interaction and the anonymity in digital spaces can diminish empathy and facilitate aggressive behaviour, such as cyberbullying. The research employs a qualitative case-study approach, involving in-depth interviews with 21 participants, including educators, policymakers and experts, as well as document analysis of national policies. The findings reveal a connection between the perceived decline in students’ empathy and a rise in cyberbullying cases. Participants emphasised the difficulties that educators face in addressing incidents occurring beyond school boundaries, despite their impact within schools. The findings underscore the complexities of cyberbullying and the role of educational technologies in enabling it. They also highlight the absence of clear policies on cyberbullying and the increasingly blurred lines between the physical school environment and digital spaces. Educators, especially teachers and school leaders, were primarily concerned with the operational challenges, while policymakers and experts focused more on the well-being of victims. The findings underscore the need for schools to extend their responsibility beyond physical premises. The study aligns with the online disinhibition effect theory, and calls for comprehensive strategies in the curriculum and school policies to address cyberbullying effectively.