Trailer positioning plays a significant role in the overall aerodynamics of a tractor-trailer combination and varies widely depending on configuration and intended use. In order to minimize aerodynamic drag over a range of trailer positions, adjustable aerodynamic devices may be utilized. For maximum benefit, it is necessary to determine the optimal position of the aerodynamic device for each trailer position. This may be achieved by characterizing a two-dimensional design space consisting of trailer height and tractor-trailer gap length, with aerodynamic drag as the response. CFD simulations carried out using a Lattice-Boltzmann based method were coupled with modeFRONTIER for the creation of multiple Kriging Response Surfaces. Simulations were carried out in multiple phases, allowing for the generation of intermediate response surfaces to estimate predictive error and track response surface convergence. These response surfaces were employed to generate an optimal positioning map for the given aerodynamic device. This methodology was further refined by obtaining positioning maps for multiple tractor configurations.