The International Regulations for the Prevention of Collisions at Sea (IRPCS) provide a comprehensive set of instructions for watchkeeping officers to follow and prevent collisions at sea. This study compares how six newly qualified deck officers and six Master Mariners, who were all trained at the same college, applied the IRPCS. Individual, semi-structured interviews were used to uncover how the 12 participants applied and interpreted the rules for three authentic scenarios. Phenomenography was used to capture the qualitatively different means by which participants interpreted the IRPCS. For basic collision avoidance situations, the results indicated little difference between the cohorts' ability to interpret and apply the IRPCS. However, when the scenarios became more complicated, Master Mariners outperformed newly qualified deck officers. In these cases, Master Mariners displayed a greater capacity to assess the overall situation, whereas newly qualified deck officers tended to simplify by focusing on a single rule. These findings indicate that training needs to focus on developing situational awareness; and training scenarios need to incorporate multiple vessels in authentic scenarios to enhance newly qualified deck officers' capacities to interpret the IRPCS.