The article reviews the ways of insurance in railway transport, namely compulsory insurance of the civil liability of the carrier for causing damage to life, health, property of passengers and voluntary insurance of passengers on the basis of the management system for passenger transportations in the automated control system “Express”. In the case of compulsory insurance, a railway ticket for a longdistance train is a confirmation that the passenger is insured. No additional documents are needed. In the case of voluntary insurance, a passenger can purchase a voluntary insurance policy at the railway ticket office or through the website www: //rzd.ru. The ACS “Express” gives the opportunity for a passenger to issue a travel document for a long distance train and a policy of voluntary insurance against accidents in one of four insurance companies: PJSC “Rosgosstrakh”, LLC “Renaissance Insurance Group”, JSC “Insurance Company BLAGOSOSTOYANIE”, JSC “Insurance Company of the Gas Industry” (SOGAZ). At the moment each insurance company offers insurance premium of 3 par values with the relevant insurance amounts. The cost of voluntary insurance policies depends only on the sum insured and does not depend on such factors as the duration of the trip, the train category or the age of the insured. Insurance coverage is valid during the trip from the moment of announcement of boarding, but not earlier than 30 minutes before departure, and ends no later than one hour after the arrival of the insured passenger to the destination station, provided that it is located on the territory of the railway station or terminal. The insurance contract is concluded for one trip in longdistance railway transport. The information technology of voluntary insurance creates for passengers more attractive conditions, the comfort and safety of passenger transportation increases. The article provides the functional description and report examples of developed and implemented in the industrial operation software and analysis complex on the basis of the ACS “Express”, which includes automated work stations (AWS) “Insurance companies and complexes”, “Voluntary insurance” and “Inquiry on insured passengers by train”. This software and analytical complex implements tasks that ensure the formation of reference and analytical information, operational financial reporting on the sold voluntary insurance policies and monitoring of the demand indicators of insurance policies and insurance companies.