Headlight leveling systems and methods are described. A determination can be made as to whether an input corresponding to a loading condition of the vehicle has been received from a vehicle occupant. If an input corresponding to the loading condition of the vehicle has been received from the vehicle occupant, a headlight level setting can be determined based upon the input. Further, an orientation of a light emitting portion of a vehicle headlight assembly can be caused to be adjusted based on the headlight level setting. Manual lookup of a loading conditions correlation table by the vehicle occupant to determine a correct headlight level setting can be avoided. In some instances, responsive to receiving a signal indirectly indicative of a potential change in a loading condition of the vehicle, a prompt can be presented to a vehicle occupant to provide an input corresponding to the loading condition of the vehicle.