Understanding the impact of technology introduction on users’ attitudes toward and behaviour with technology is increasingly important. This paper suggests several research questions that are important as Wearable, Immersive Augmented Reality (WIAR) systems are introduced in ship navigation: what contributions to navigation decision-making might be made by WIAR technology? And how do these influences relate to safety in marine transportation? This paper begins with an overview of information needs for shipboard navigation and piloting, and then describes the evolution of shipboard decision support systems for navigation, including the emergence of wearable, immersive augmented reality systems. An assessment of piloting and navigation information needs and the capabilities of WIAR are then presented, which suggests a conceptual model for studying the impact of WIAR systems on performance and safety in marine transportation. Conclusions and future work to explore the role and contribution of WIAR technology to the safety of navigation are then presented.