Since the late eighteenth century, the Russian Empire had had free reign in its territorial expansion around the Black Sea, in the direction of Constantinople and the Eastern Mediterranean. That geopolitical design struggled, however, to co-exist with the new European order of Vienna, of which Russia had been a chief promoter. The treaty of the Holy Alliance (September 26, 1815) sponsored by Tsar Alexander I, which established a supra-denominational Christian order in Europe, conspicuously relegated the territories of the Muslim Sultan as a “grey area” for the ius gentium. To make things worse, the Sublime Porte was absent from the peace negotiations of Vienna. This paper will argue that the highly paradoxical attitude of Russia toward the Ottoman Empire was a determining factor in the emergence of the explosive Eastern Question. There lied an “Achilles’ heel” that would eventually spell the demise of the order of Vienna, culminating in the disaster of the Crimean War (1853-56).