Determination of the impact of failures of automation devices to the losses during the transportation processes for the current economic conditions is one of the most urgent tasks, the solution for which will allow to improve the service technology and to develop absolutely new approaches to the station and spans furnishing with automation devices. The methodology of resource and risks management and the methodology of reliability analysis as well as approach within which the simulation is applied allow to solve this problem for the purpose of the mainline railway transport. The article demonstrates the approaches for assessing the damage to the transportation process under failures of railway automation devices. Thanks to simulation the samples of station performance were obtained, including the average of carriage inactivity and the total delay. The random component in the timetable of reception and departure of trains, as well as in the duration of technological operations results in random nature of station performance. The article provides that it is impossible to talk about definitive increase of technological losses in case of failure of railways automation and remote control devices because of the significant impact of train flow fluctuations and decisions, made by operational management personnel. The article also proposes a method, that allows to estimate the probability of increasing the losses as well as the risk of economic losses due to the failure.