To investigate the feasibility of various aerodynamic test procedures for the Phase 2 Greenhouse Gas (GHG) Regulations for heavy-duty vehicles in the United States, the US Environmental Protection Agency conducted, through Southwest Research Institute (SwRI), coastdown testing of several heavy-duty tractors matched to a conventional 53-foot dry-van trailer. Three vehicle configurations were tested, two of which included common trailer drag-reduction technologies. Air speed was measured onboard the vehicle, and wind conditions were measured using a weather station placed along the road side. Tests were performed on a rural road in Texas. One vehicle configuration was tested over several days to evaluate day-to-day repeatability and the influence of changing wind conditions. Data on external sources of road forces, such as grade and speed dependence of tire rolling resistance, were collected separately and incorporated into the analysis. Various statistical and mathematical techniques are discussed in relation to challenges associated with using coastdown data to determine aerodynamic drag, including uncertainty, yaw angle determination, and asymmetry due to direction of travel.