The efficiency of organising freight transport and using motor transport in a Smart City depends on a set of its properties, which in the process of operation determine its suitability for use in given operating conditions. Vehicles have different overall dimensions and designs, which determine their maneuverability and directional stability, their ability to make a curve-line movement in the city, as well as to move safely in reverse. Nowadays, tractor-trailer combinations with non-turning semi-trailer wheels are widely used for freight transport. Such a scheme of vehicle construction does not ensure its directional stability when reversing, which can lead to the folding of the tractor and semi-trailer and loss of mobility of the combination. In the absence of additional special systems, the driver controls the rearward movement of the road train using the steering wheel and rear-view mirrors, and the accuracy of delivery to the object depends on the level of the driver's training. The research of driver's reaction time spent on situation assessment, decision making, and realisation has been carried out. It has been revealed that with manual control, there are difficulties connected with training of drivers to estimate the parameters of movement and control of the road train, in particular, with the process of parking and its accurate delivery to the object. With the help of the developed mathematical model of the rearward movement of the road train and the proposed new turn control law, the research of maneuvering of the road train during its delivery to the object has been carried out and the results confirming the possibilities of building an automated system allowing to reduce the influence of the human factor on the parking process, as well as to reduce the time required to perform the maneuver have been obtained. The conducted analysis of system stability with the help of Routh–Hurwitz criterion has determined the conditions of providing stability of the system moving in reverse. The method of controlling the backward movement of the road train and the design of the device realising it has been developed. The results of simulation modeling allowed us to find the necessary values for the control law for the movement of road trains of different lengths, as well as the preferred variants of the initial positions of the road train for the realisation of its precise delivery to the object.