The problem of dynamic fleet management for truckload carrier fleet operations is introduced, and the principal elements of a simulation framework for the evaluation of dynamic fleet management systems are described. The application of the simulated framework to the investigation of the performance of a family of real-time fleet operational strategies, which include load acceptance, assignment, and reassignment strategies, also is described. The simulation framework described is an example of a first-generation tool for the evaluation of dynamic fleet management systems. Selected experimental results are highlighted. These are intended to illustrate some of the issues encountered in real-time fleet management and the role of the simulation modeling environment in investigating them.