The objective of this paper is to evaluate the dynamic performance of pickup truck - trailer configurations, using performance measures adopted by Commercial Vehicle Safety and Enforcement (CVSE). The pickup truck models are selected based on the US truck classification that segregates trucks on the basis of the vehicle’s gross vehicle weight ratings (GVWR). Three different types of trailers - gooseneck trailer, pintle hook trailer and three-axle trailer with parametric hitch - are utilized in this study. The truck-trailer configurations will be evaluated for static rollover threshold, load transfer ratio, rearward amplification, friction demand, lateral friction utilization, high speed, low speed and transient off tracking and three-point handling performance. These measures are based on definitions from Canada’s heavy vehicle weights and dimensions study. Payload weights and trailers are selected based on the current British Columbia regulations, maximum towing capacity of each pickup truck, and their maximum drive axle loads. The main purpose of this analysis is to computationally evaluate the stability and controllability of these vehicle configurations in a virtual environment at both low and high speeds. TruckSim - a commercial software package that predicts the dynamic performance of multi-axle vehicles in complex scenarios - will be utilized in this study. This software was developed to predict the directional and roll response of single and multiple articulated vehicles that approach rollover situations. This package has been extensively used by the industry to evaluate and validate various heavy vehicle configurations.