With increasing emphasis on new soft mobility in urban areas, it becomes more and more important to provide effective speed control measures for vehicular traffic. Among those, the ones based on vehicle vertical deflection, namely vertical traffic calming measures, are historically the most widespread. However, since the basic operating principle of these devices is related to the vertical dynamic response due to the interaction between the moving vehicle and the road profile, different vehicles may exhibit different speed behaviors when traveling on a specific road profile shape. As a matter of fact, recent research provided evidence of this connection, and therefore it has been worth investigating the dynamics underlying the phenomenon in order to develop a new approach to the design of vertical traffic calming devices. In this paper, following an initial state-of-the-art review, an in-depth study on the dynamic interaction between vehicle and road profile has been presented by means of an ad hoc-developed mathematical model. The proposed simulation model has been used to evaluate the root mean square acceleration value associated with each vehicle/traffic calming device/crossing speed. Following the outcomes provided by numerical simulations, an experimental investigation has been designed and carried out on a vertical traffic calming device. Speed profiles of different vehicles have been acquired, and preliminary results seem to provide evidence of a different dynamic response for each vehicle type, yielding the basis to reconsider the design approach of such devices in order to control urban traffic speed.