The study focuses on analyzing the impact of digital technologies and customer orientation on railway transport, emphasizing the need to integrate modern technologies, increase environmental friendliness, and develop individualized approaches for passengers. Key aspects of passenger and freight transportation, such as pricing, comfort, punctuality, safety, and service availability, are identified, with an emphasis on the importance of multimodal transportation and energy-efficient solutions in the rail transportation segment. An integrated approach for assessing the level of development of customer-oriented railway transport is formulated, based on two main components: the construction of a synthetic (integral) indicator that encompasses several partial (not directly comparable) key parameters affecting passenger satisfaction and service efficiency, as well as the application of an integrated ARIMA autoregression model for predicting future customer satisfaction and rail transport service quality. A comprehensive analysis of modern trends and methods for assessing the level of customer orientation in railways, which can be used for the development of the transport sector of the country’s economy, is proposed.