Military personnel involved in convoy operations are often required to complete multiple tasks within tightly constrained timeframes, based on limited or time-sensitive information. Current simulations are often lacking in fidelity with regard to team interaction and automated agent behavior; particularly problematic areas include responses to obstacles, threats, and other changes in conditions. More flexible simulations are needed to support decision making and train military personnel to adapt to the dynamic environments in which convoys regularly operate. A hierarchical task analysis approach is currently being used to identify and describe the many tasks required for effective convoy operations. The task decomposition resulting from the task analysis provides greater opportunity for determining decision points and potential errors. The results of the task analysis will provide guidance for the development of more targeted simulations for training and model evaluation from the driver’s perspective.