It is broadly assumed that attempts by the Russian state of Muscovy to establish stable diplomatic and mercantile channels to India via Central Asia were started upon the initiative of the Emperor Peter I (1682–1725). Such attempts are generally interpreted as being part of a large-scale project that reflected the growing imperial and colonial ambitions of Russia and which, in turn, entailed strong antagonism from the ruling elites of Central Asia, thereby setting a tone for relations that would continue for the next century and more of reciprocal relations between the local principalities and Russia. By exploring chancellery documents from seventeenth-century Muscovy, we find that the first diplomatic communications between Russia, Khiva, and Bukhara can in fact be dated to long before the reign of Peter I. The first Romanov tsars sought to initiate exchanges with Khiva and Bukhara as a means of establishing diplomatic and commercial ties with the Mughal emperors; at the same time, meanwhile, the authorities in Khiva and Bukhara had their own reasons for pushing Muscovy to engage with Central Asia as a conduit to India. Over the course of the seventeenth century, Central Asian diplomats went to great lengths—both in diplomatic correspondence and through direct interpersonal contacts—to convince their Russian counterparts of the region's attractiveness as a source of precious Indian commodities and as a logistically convenient passage to India. Despite such rhetoric, however, the authorities in Khiva and Bukhara were in fact highly reluctant to “open” the region to Russian agents: repeated attempts by Muscovy to engage in diplomatic fact-finding as a means of establishing influence in the region invariably foundered in the face of Central Asian resistance. Bukharan and Khivan circles seem, in fact, to have held out the enticing idea of “a passage to India” simply as a rhetorical device to secure recognition in Muscovy for their own diplomatic and mercantile missions.