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Digitization is reshaping the maritime industry which is under increasing pressure to transform. Technology is more common as it offers improvements and carves out early adapters as more competitive. COVID-19 hastens digitization and creates new digital opportunity structures which increase cyber risks. Cyber attacks, which can cripple critical systems and services at significant cost, motivate stakeholders to engage with these risks. This paper reviews current events and introduces an exercise where participants at a NATO Centre of Excellency were shown scenarios involving maritime cyber incidents and evaluated on cyber risk perception. Our findings lend insight on how to assess group cyber risk perception—and how this impacts response. They highlight the need to plan for cyberspace operations and ground cyber risks as a intricate governing factor in maritime.