Nowadays, more-and-more cyber-security training is emerging as an essential process for the lifelong personnel education in organizations, especially for those which operate critical infrastructures. This is due to security breaches on popular services that become publicly known and raise people’s security awareness. Except from large organizations, small-to-medium enterprises and individuals need to keep their knowledge on the related topics up-to-date as a means to protect their business operation or to obtain professional skills. Therefore, the potential target-group may range from simple users, who require basic knowledge on the current threat landscape and how to operate the related defense mechanisms, to security experts, who require hands-on experience in responding to security incidents. This high diversity makes training and certification quite a challenging task. This study combines pedagogical practices and cyber-security modelling in an attempt to support dynamically adaptive training procedures. The training programme is initially tailored to the trainee’s needs, promoting the continuous adaptation to his/her performance afterwards. As the trainee accomplishes the basic evaluation tasks, the assessment starts involving more advanced features that demand a higher level of understanding. The overall method is integrated in a modern cyber-ranges platform, and a pilot training programme for smart shipping employees is presented.

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