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International interest in Maritime Autonomous Surface Ships (MASS) is on the rise. This exploratory research presents insights of a sample of licensed deck officers (LDOs) regarding the potential future of the Collision Avoidance Regulations (COLREGs) with the implementation of MASS. At present, there is much discussion in the maritime industry on if and how the COLREGs will need to be amended to be able to be applied to MASS. Limited research is published from the key perspective of the LDO. Qualitative and quantitative methods are used, including a literature review and a multiple-choice survey. Data is analyzed via descriptive statistics, and commonalities within the results are investigated as well as years of experience with practicing the COLREGs. Results show that many barriers exist when applying the COLREGs to MASS, and minor amendments to certain terms and definitions are recommended. Moreover, the COLREGs should not be quantified, and MASS should be identifiable from other vessels. LDOs with more experience with practicing the COLREGs are found to be slightly more open to changing the rules versus LDOs with less experience. When compared to the results of the International Maritime Organization’s regulatory scoping exercise, the results of this study are found to be in congruence. This research provides valuable insights for the ongoing discussion of the future of MASS operation in the maritime industry.