In an effort to develop tools to help address various aspects of heavy truck size and weight impacts on pavements, bridges, truck safety, and economics, the Roads and Transportation Association of Canada undertakes research to look at the feasibility of applying expert system technology to various aspects of this problem. A prototype expert system capable of assessing the legality of various truck configurations was also developed. The problem definition stage of the work required much greater effort than originally anticipated. Expert systems were found to be applicable in the areas of generating alternative regulations, dealing with operational problems within motor carrier fleets, and in the interpretation of regulations. In other areas, the need for conventional and “hybrid” tools was found. The prototype system addressed the subproblem for which it was conceived, although simplifications were required to achieve this goal within the original budget.