This paper investigates the interaction between vehicle dynamics parameters and road geometry during the passing process. The methodology is based on a realistic representation of the passing task with respect to roadway’s posted speed and the ability of the passing (examined) vehicle to perform such maneuvers. Regarding passing distance outputs, an existing vehicle dynamics model was utilized, where aiming to assess the model’s accuracy, instrumented field measurements were performed. The analytical model is computationally demanding. Therefore statistical models were worked out, in line with the German rural road design guidelines, to determine passing sight distances (PSDs) by arranging combinations of 4 critical vehicle—roadway parameters; namely, vehicle horsepower rates, variations between the passed vehicle’s speed and roadway’s posted speed, peak friction supply coefficients and grade values. The analysis revealed that the difference between the speed of the passed vehicle and the posted speed value, as well as certain interactions of the assessed parameters impact excessively PSD, especially for values below 20 km/h. The lognormal modelling approach for predicting PSDs was found efficient and may be useful to researchers and practitioners aiming to evaluate the interaction of the utilized road—vehicle parameters in terms of determining PSDs as well as passing zones. Although more advanced communication between vehicles or between vehicles and road environment seems a prerequisite in order integrated guidance during passing maneuvers to be enabled, the present research consists an opening paradigm of how the passing process can be standardized and therefore deployed in advanced driver assistance systems (ADAS).