The Russo-Turkish stand-off, which began under Ivan IV the Terrible, was largely motivated by the rising imperialism and ambitions of Muscovy, which the no less ambitious Ottoman sultans, who in turn were expanding their Ottoman Empire, wished to oppose in order to maintain and extend their influence also in the Black Sea, Caspian regions and the Caucasus, where Russian troops were slowly ‘infiltrating’ and to which Moscow’s foreign policy was also increasingly turning its attention. Tsar Ivan IV conquered and destroyed all the Tatar states (including Astrakhan, Kazan, the Siberian Khanate, the Nogai Horde), with the exception of Moscow, which was increasingly subjected to the Russian occupation. Although he eventually achieved military supremacy over Crimea, Ivan IV was unable to subdue Crimean Khanate. In order for Crimea to survive, the Crimean Khan had to accept in the 1580s that Crimea, already formally a vassal of the Ottomans since 1474/1475, would become even more dependent on the Ottoman Empire. This article examines Ivan the Terrible’s eastern policy ambitions, as well as Muscovy’s relations with the khanates, especially the Khan of Crimea, and the diplomatic correspondence between the rulers (the Khan of Crimea and Ivan IV). In addition to excerpts from the letters of the various khans and the Russian tsar’s replies, we present commented translation into Estonian of a letter of 1572 from the Crimean khan Devlet-Girei to Ivan the Terrible, about a year after his raid on Moscow and just after the Battle of Molodi in the summer of 1572. More recently, the history of Russo-Tatar-Turkish relations has shown that the existence of the Crimean Khanate in the 17th and 18th centuries depended to a large extent on the support of the Turkish Sultan, and that eventually, after a series of Russo-Turkish wars (often involving Crimea), the Russian Empire absorbed the Crimean Khanate. Admittedly, this took place 200 years after the death of Ivan IV, in 1783, when the Russian Empire was ruled by Catherine II. However, it was Ivan IV who laid the foundations for the conquest of the Tatar lands, and this was only the first episode in a series of Russian-Turkish wars and the Russian-Turkish confrontation, which in fact continues to some extent to this day.