During the reformation of the railway and creation of its economic security, it is critical to study the organizational and economic fundamentals of the coverage of railway enterprises and define characteristic of formation of insurance relations between the railway enterprises and insurance companies. Improving the quality of insurance of the rail transport requires defining a legal framework regulating the coverage of railway enterprises, as well as presence of supervisory and control organisations that manage the implementation. Such organisations require a comprehensive application of financial, economic and organizational methods of regulation of relations in the relationship “railway company – insurer”. This study aims to disclose the organizational and economic fundamentals of the formation of the system of insurance protection of railway enterprises and to identify the areas for improvement in the process of activation of the reformation of the railway transport. In order to achieve this goal, we outlined the characteristics of the formation of insurance relations between the railway and insurance companies and define the fundamental rules to be followed in the process of cooperation. To ensure the implementation of the proposed railway insurance framework, we suggest to create an office for securing the rail transport, which, by using alternative methods, forms and presents a package of requirements for governing related services to a potential insurance company. We propose the main criterion for the selection of the foundation of the office to be the readiness to satisfy the needs of a transport operator and consider the implementation of an individual approach for providing insurance services.