Abstract Introduction: Remote Operating Centers (ROCs) enable human oversight of remotely operated and autonomous ships. However, the “human-in-the-loop” model of automated control oversight implies prolonged periods of inactivity punctuated by safety-critical action. This paper investigates the extent to which this role is aligned with humans’ innate attentional resources in terms of boredom, vigilance, and repetition. Method: A simulator study was completed with ROC operators (volunteer participants with relevant expertise). One group completed a short scenario (5 minutes; N = 16); the other completed a long scenario (30 minutes; N = 16). The duration marked the onset of a stimulus (an alarm), prompting manual takeover. In a mixed method approach, four sources of data were collected, consisting of pupillometry, questionnaire, interview, and video data. Results: Pupillometry data showed larger pupillary constrictions in the 30-minute group, indicative of decreased cognitive activity (effect size 0.25 mm). The questionnaire showed that operators in the 30-minute scenario were more likely to experience their tasks as unchallenging, understimulating, and lacking in meaning. Finally, a relationship was found between repetitive content and varying perceptions of time duration. Moreover, operators perceived scenarios as longer when they detected an “oddball” in the repetitive series (a gorilla passenger). Conclusion: ROC work as currently imagined is prone to boredom, vigilance decrement, and suppression of repetition. The study adds to the empirical research about boredom and its associated cognitive states in control room work. The study also contributes to design considerations impacting safety and organizational aspects like operator training and retention.