The combination of pavement rutting, poor road alignment, and extreme adverse weather will seriously threaten the driving safety of vehicles, whereas only a few of these factors are commonly concerned. This study aims to efficiently evaluate the impacts of various driving conditions on the lateral stability of the vehicle and produce a practical recommendation for pavement maintenance in what concerns rutting. A systematic framework was, thus, developed to conduct a comprehensive evaluation of the lateral stability of the vehicle, which incorporates a single-factor test and multi-factor test based on the stability indicators obtained from Carsim simulations. The vehicle road weather model was established in the Carsim software by considering seven factors, including driving speed, width–height ratio (WHR) of rutting sidewall, radius of circular curve, superelevation, crosswind angle, crosswind speed, and friction coefficient, respectively. The results show that the established framework behaves with satisfactory performance, regarding evaluating the effect of various impact factors on the lateral stability of the vehicle while driving across rutting. Stability indicators suddenly fluctuate in a short time, due to the instantaneous wandering behavior of crossing rutting. Additionally, the sudden fluctuation phenomenon is greatly enlarged, and the vehicle is inclined to occur with lateral instability when WHR equals 5, particularly in roll-over instability. It is recommended to concurrently confine the WHR greater than 10 and friction coefficient greater than 0.4, in order to ensuring driving stability. The multi-factor test revealed that the vehicle speed and WHR of the rutting are leading factors that affect driving stability, followed by the radius of circular curve, superelevation, crosswind angle, crosswind speed and friction coefficient, respectively, which are both essential factors for driving stability. The outcomes of this study may contribute to supplying guidelines for controlling key adverse conditions and making decisions on pavement maintenance.