Many industries struggle with training dynamic risk assessment, and how to bridge the gap between safety training and behavior in real life scenarios. In this article, we focus on dynamic risk assessment during a mooring operation and investigate the potential value of using immersive virtual reality (VR) simulations compared to standard training procedures in an international maritime training organization. In a pilot study, we compared two ways of implementing a VR simulation (stand-alone or with post-simulation reflection) to a manual and a personal trainer condition in a between-subjects design with 86 students in a maritime school. Based on the results we compared the stand-alone VR simulation to the personal trainer condition in a between-subjects design in a non-Western, Educated, Industrialized, Rich, and Democratic (WEIRD) sample of 28 seafarers from the Kiribati Islands at an international maritime training organization. The VR simulation group reported significantly higher perceived enjoyment (d = 1.28), intrinsic motivation (d = 0.96), perceived learning (d = 0.90), and behavioral change (d = 0.88), and significantly lower extraneous cognitive load (d = 0.82) compared to the personal trainer group, but the differences in self-efficacy, and safety attitudes were not significant. The results support the value of using VR to train procedures that are difficult to train in the real world and suggest that VR technologies can be useful for providing just in time training anywhere, anytime, in a global market where employees are increasingly cross-cultural and dislocated.