Since donning the mantle of authority, President Putin has taken actions which have uninhibitedly been geared at reasserting Russia’s hegemony around the world. Putin’s Look East policy stems from his schematic geopolitics, a plan which was formally announced in 2010. Through the prism of Putin’s Look East policy, the paper contextually analyses Russia–South Asia relations, with reference to India and Pakistan. By cross-examining Russia’s official foreign policy documents, the paper establishes why South Asia is paramount to Russia’s economic and geostrategic reassertion. Every new policy has its challenges, and the same holds true for the Look East policy vis-à-vis South Asia. Premised on the unfolding geopolitics in the region, the paper surmises that striking a balance between New Delhi and Islamabad will be problematic for Moscow, just as it has always been for Washington.