This article is devoted to the study of the entropic orderliness of road safety systems of various dimensionalities. The author’s methodology for quantitative assessment of the quality of the road safety systems is based on the use of information entropy analysis, the essence of which is to assess the significance (or “weights”) of various information-technological stages of the road traffic accident rate formation process. The main emphasis in this paper is on the philosophical interpretation of the results of entropic evaluation of the orderliness of urban road safety systems. The article aimed to philosophically understand the reasons for the diversity in the results of assessing the entropy of road safety (RS) in Russian cities. Within the framework of this goal, the results of the analysis of the state of the issue, ideological approaches and methods for assessing the relative entropy of urban road safety systems were presented. The study was based on analyzing statistics that characterize the processes of the formation of road traffic accidents in Russian cities classified into three groups based on population size. The experimental results obtained were explained from the point of view of human psychology. Rather, results were explained from the perspective of human psychology. The final results of the study once again illustrated the objectivity of Hegel’s dialectical laws and, perhaps, once again shattered illusions about the possibility of achieving high levels of road safety in cities by building rigid systems to regulate the actions of traffic participants. In the author’s opinion, the results of the presented philosophical analysis will be useful to managers specializing in the management of complex systems (not only transport but also other fields) to comprehend the contradictions of the complex nature of humans and the paradoxes of their behavior when their freedom of action is restricted through external control.