Information warfare and security are crucial to maintaining homeland security. An important mission of the information warfare force is to ensure that secure information and facilities are well protected. One way to ensure this is to try to gain access to this information as outsiders and see how well the practices and policies designed to protect data are being enforced. Teams of Information Warfare personnel (a.k.a. the Red Teams) are dedicated to the mission of testing the security of information and assets crucial to American interests. Most such missions necessitate deception in order to test the extent to which data is protected from strangers and parties who are not trusted. High-levels of stress are inevitable, and the Red Teams need to be highly skilled in thinking creatively under such stress. Given the criticality and the degree of danger of these missions, they have to be carefully trained. For computer-based approaches, providing realistic simulations is essential for successful training. Engaging the trainee emotionally to elicit the types of stress responses they will experience on real missions is crucial. 3D computer games have proved themselves to be highly effective in engaging players motivationally and emotionally. This effort, therefore, uses gaming technology to provide realistic simulations. These games are augmented with Artificial Intelligence techniques for enabling trainees to interact with the simulation using natural language, intelligent evaluation of the student's performance, and automated after-action review that allows the trainees to assess their own performance and provide justifications for their actions. This paper describes the details of this approach, providing examples of the simulations and after-action reviews, and discusses its benefits and limitations.