As the maritime industry rapidly digitalises, robust cybersecurity measures have become essential. This chapter presents an innovative approach to cybersecurity awareness training for future seafarers, focusing on integrating behaviour change models to enhance cyber resilience. By addressing the cybersecurity challenges inherent in modern maritime operations, it proposes a framework for embedding these models into maritime education, transforming training from purely informational to behaviourally transformative. A key concept introduced is the “level of paranoia,” denoting a heightened state of vigilance that encourages seafarers to be more cautious of cyber threats without causing undue fear. Improving this appropriate level of paranoia enables future maritime officers to better detect and respond to cybersecurity risks. A case study from TalTech Estonian Maritime Academy demonstrates the practical impact of this approach. The academy implemented a compulsory “Introduction to Cybersecurity” course incorporating the COM-B model and Fogg’s behaviour model to foster secure habits among students. This led to increased understanding of cyber threats and the adoption of long-term secure behaviours, evidenced by improved responses to simulated cyber incidents and positive feedback on habit-forming exercises. The chapter offers valuable insights and practical strategies for reshaping maritime cybersecurity education to meet the demands of the digital age. It underscores the necessity of cultivating a security-conscious culture among future maritime officers and demonstrates the effectiveness of behaviour-focused training in enhancing the industry’s overall cyber resilience.