The author analyzes the impact of the globalization processes on the Russian regions as they enter the international system of regions. Three key challenges are singled out and discussed in detail. The first one is related to the fact that the countries of the West have not yet made up their minds as to their strategy (strategies) with respect to Russian reforms. The author evaluates the state of the Western “expertise” of Russian regional development, as well as the interaction of scientific conclusions and political practice. The second challenge seems to the author to consist in that the stratification of Russian political space has resulted in the appearance of different views of the prospects for international integration of Russian Federation. Finally, at the level of regions themselves, there exist different interests in the sphere of international cooperation, and differing strategies of their realization.