Recent maritime cybersecurity accidents reveal that shipping is facing increased exposure to cyber threats, especially due to the fast-growing digitalisation of the sector, leaving vessels and their onboard systems vulnerable to cyberattacks. This research aims at evaluating the relationship among the critical dimensions influencing cybersecurity performance in the maritime industry. To achieve this, six critical dimensions related to cybersecurity preparedness are first identified through literature review, namely ‘regulations’, ‘company procedures’ from a managerial perspective and ‘shipboard systems readiness’, ‘training and awareness’, ‘human factor’ and ‘compliance monitoring’ at an operation level. A Likert-scale questionnaire is designed and used to collect empirical data from 133 seafarers and shore-based staff. Structural Equation Modelling (SEM) is applied to examine the causal relationships between the six dimensions and shipboard cybersecurity performance. The results show that ‘regulations’ positively influence shipping companies’ cybersecurity-related ‘procedures’, which in turn positively affects ‘shipboard systems readiness’, ‘training and awareness’, and ‘monitoring’. Further, ‘training and awareness’ positively influences the cybersecurity performance of ships. The results have profound implications for the shipping industry on how to strengthen their cyber practices in order to improve their cybersecurity performance. Recommendations for future academic research related to maritime cybersecurity are also provided.