The first 18 months of Vladimir Putin’s presidency turned out to be a period of unprecedented activity in Russian–Ukrainian relations. A number of problems were seriously approached, among these the issue of Ukrainian gas debts. At the same time, it remains unclear whether the new cooperative dynamics will prevail or whether the conflictual legacy of the 1990s will become an insurmountable impediment to further improvement. This article attempts to analyse the factors which determined the ongoing evolution in Russian–Ukrainian relations in order to demonstrate that the positive dynamics had to do with changes in the views of the Russian leadership and in the export strategies of Russia’s big businesses, as well as the evolution of Ukraine’s posture vis-à-vis Europe, rather than with the internal political situation in Ukraine in 2001. The article also examines the main remaining controversies between the two countries in the economic and humanitarian spheres and offers a view on whether reciprocally pragmatic approaches are possible.