Practice and experience are fundamental to seamanship and shiphandling training, but are significantly limited by platform availability and at sea time. With hands-on experience and at-sea assignments available only to a subset of personnel at a given time, virtual environments (VEs) have the potential to provide a complementary and cost-effective method to support task mastery without putting lives and platforms at risk. VE training systems, such as the Conning Officer Virtual Environment (COVE) currently used by the US Navy for training ship-handling skills, have great potential value to increase training exposure. However, even these virtual systems are resource-intensive because they require highly trained instructors to closely monitor individual students’ progress and provide targeted coaching and feedback. The growing popularity of VE-based training approaches is rapidly outpacing the number of available instructors, who need better tools to support their delivery of high-quality training to larger numbers of students. In this paper, we describe ongoing research and development efforts to extend the Navy’s VE training capabilities by creating work-support tools and dashboard displays that enable COVE instructors to efficiently monitor and manage larger numbers of students with VE training. Based on design principles that support attention management, we have created a series of linked alerting displays to support improved instructor supervision across multiple student training sessions. We also present our analytic approach, provide design implications and initial instructor support concepts, and discuss how our approach and initial results are generalizable to other VE-based instructional settings.