Game-based simulations are being designed to portray the immersive experience of live role-play while providing a cost-effective, visually compelling, and easily accessible medium for military training. In this article, we discuss issues involved in using role-play for cultural training and describe a pilot study comparing live role-play versus role-play in a recently developed simulation environment. Developers of training involving role-play should realize (a) the importance of proper preparation for all involved and (b) the significance of the game-based interface in allowing the user to be able to convey and appreciate the cultural and interpersonal aspects of the interaction.