For almost three centuries, starting with the campaign of Peter the Great in 1721–1722, Russia has traditionally played a key role in the Caspian Sea. The situation changed dramatically with the collapse of the USSR in 1991 and the emergence of three new regional players-Azerbaijan, Kazakhstan and Turkmenistan. For Russia, this meant a significant reduction in influence in the region and the loss of control over most of the water area and the sea and its resources. In the historiography devoted to the region, the emphasis is placed on assessing the new round of geopolitical struggle, the position and interests of Western and regional powers. The author of this article provides a critical analysis of changes in Russian policy towards the Caspian Sea over the past 30 years and assesses the effectiveness of these changes. The difficult transition from the role of a dominant player in a region closed to external competitors to an open geopolitical confrontation over resources, their transportation routes, and political influence at the first stage was not in favor of Russia. Russia could not defend the principle of a condominium for joint development of hydrocarbon resources of the sea. With the active assistance of Western competitors, Russia lost its status as a monopoly transit country for oil and gas from the region. At the same time, thanks to diplomatic efforts and increased political dialogue with its neighbors in the region, Russia managed to resolve all territorial issues at sea by 2003, maintain the closed status of the sea for the military forces of third countries, and by 2018 complete work on the Convention on the international legal status of the sea, which established the principles of cooperation in the region that are important for the Russian Federation. Thus, official Moscow managed to achieve the strategic goals adapted after the collapse of the USSR by using the traditional strengths of its foreign policy and consolidate its status as the most influential player in the region.