The railway sector is an important part of the transportation industry as well as of the economic activity in Europe. It is interesting that digitalization of this sector has been triggered in several European countries by regulatory compliance obligations. The Technical Specification for Interoperability relating to Telematics Applications for Freight/Passenger Services as well as other related standards have created opportunities for the digital transformation of the players participating into this market. Apart from achieving a base minimum compliance to the standards, there are prerequisites and questions to be answered at organizational and technological level if railway sector players are to embark on the digital transformation journey. This research study provides explanations on the argument the regulatory compliance may act as a driver for digital transformation, using the example of the railway sector in Europe and presents some important prerequisites for this market’s players to take the opportunity for digital transformation. The ultimate goal of this research, whose foundations are set up in this research paper, is to formulate a digital maturity model for the actor of the railway sector, for the benefit of their retail and business clients.