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In this chapter, the focus is on cybersecurity training and the continuous adaptation of training programs, emphasizing the need for dynamic, model-driven educational frameworks that integrate pedagogical best practices with security threat models. The chapter outlines a detailed methodology for designing, implementing, and assessing cybersecurity training—illustrated through a smart shipping use case—and demonstrates how platforms like THREAT-ARREST can tailor training to specific organizational needs while continuously monitoring and improving trainee performance.