A system and method of controlling a vehicle with a trailer comprises determining the presence of a trailer, generating an oscillation signal indicative of trailer swaying relative to the vehicle, generating an initial weighted dynamic control signal for a vehicle dynamic control system in response to the oscillation signal, operating at least one vehicle dynamic system according to the dynamic control signal, and thereafter, iteratively generating a penalty function for the weighted dynamic control signal as a function of the oscillation signal response. A neural network with an associated trainer modifies the dynamic control signal as a function of trailer sway response.