Simulation-based training offers the potential for relatively low-cost training available at any time and almost any duty station. However, a main drawback of simulation-based training is the lack of oversight in the training process. Simulations often depend on a fixed number of pre-defined training scenarios that are designed to test training objectives but not to deliver a training experience customized to the specific trainee's current level of skill and understanding. In this paper, we introduce the Interactive Storytelling Architecture for Training (ISAT), which uses an intelligent agent, the director, to assemble training scenarios that test the skill level of individual trainees. The director also provides indirect feedback about trainee actions during the execution of a training scenario, subtly adapting the training environment to stress unmastered skills and suggest remediation. This approach results in a training experience that is specialized to the trainee's individual needs and potentially more engaging, resulting in faster development of trainee proficiency.