As part of the United States Department of Energy's SuperTruck program, Volvo Trucks and its partners were tasked with demonstrating 50% improvement in overall freight efficiency for a tractor-trailer, relative to a best in class 2009 model year truck. This necessitated that significant gains be made in reducing aerodynamic drag of the tractor-trailer system, so trailer side-skirts and a trailer boat-tail were employed. A Lattice-Boltzmann based simulation method was used in conjunction with a Kriging Response Surface optimization process in order to efficiently describe a design space of seven independent parameters relating to boat-tail and side-skirt dimensions, and to find an optimal configuration. Part 1 concerns a fully-skirted tractor-trailer system, and consists of an initial phase of optimization, followed by a mid-project re-evaluation of constraints, and an additional period of optimization. The most influential parameters are identified in achieving significant aerodynamic drag reduction relative to a base configuration. Part 2 uses a similar set of optimization parameters, but finds a fundamentally different drag response to one critical factor, due to a different set of trailer operational constraints using only partial skirting. Results from both portions are supported by physical testing.