Siberian transport corridors, especially river systems, provide transit freight traffic from Asia to Europe from the 18th century. Even in the 19th century, a unique geographical position of Russia contributed to the organization of different projects concerning transcontinental logistic corridor linking the Siberian rivers and their canals. The article presents a comparative analysis of the conditions for ensuring transit traffic along the Siberian rivers in the late 19th century. The example is the construction of the Ob-Yenisei Canal in the current economic situation in Russia. The author attempts to answer the question whether the reasons that put river transport in the "high-risk group" are systemic, historical, or they are the consequence of wrong management at the end of the 20th century. The purpose of the article is to determine the level of solutions or solvability of the problems that hindered the development of water transport in the late 19th-early 20th century. In addition, the authors are trying to evaluate the competitiveness of river transport in the modern conditions of increasing pressures on Siberian transport infrastructure. The paper identified three clusters of the systemic problems of Siberian water transport-design-technological, organizational and natural-geographic. The results have shown that the solution of technological and management issues, as well as lower costs of operation of water transport did not lead to an increase in the volume of traffic freights along the Siberian rivers. Economic, natural and geographical factors became the most important for the solution of technical problems.