Growth of railway container transportation volumes in the Russian Federation obliges to pay attention to ensuring the safety of cargo transportation. In this regard, it is advisable to outline organisational and technological aspects of transport of especially valuable cargo in rail containers.The analysis of current regulatory and technical documents, domestic and foreign experience, allowed identifying the most effective areas of ensuring safety of transported goods, which are based on making changes to the design of the automatic coupling device of the rolling stock.The paper substantiates the need to use indicators of careful handling, impact, tilt of cargo, vibrations, and temperature as well as the need to revise the insurance system for transportation of goods by rail.This article describes a review and analytical study of the issue of ensuring safety of transportation of especially valuable cargo by rail, through the use of basic (making changes to the design of the rolling stock) and related (use of indicators (sensors) and improving the cargo insurance system) technical and organisational measures.