In 2006 the United States Navy will acquire four new Vertical Flight Deck Training Systems (VFDTS) that combine virtual reality simulation of helicopter shipboard landings, takeoffs, and over-deck operations with an automated Hand Signal Recognition System (HSRS), effectively transforming how and where initial helicopter signaling skill acquisition and refresher training before or between deployments can be conducted. In this paper, we describe the development and evaluation of the HSRS and discuss training issues and challenges faced by the project team. We identify instructional design issues and suggest some future HSRS capabilities and applications. Finally, we discuss links to the Department of Defense Training Transformation Initiative.