From the Muscovites’ annexation of the nearby Khanate of Astrakhan in 1556 to their expulsion from the region by the Ottomans and their allies in 1605, the North Caucasus was a contested borderland. This book considers the poorly understood first encounter between the Ottoman Empire and the Tsardom of Muscovy, drawing on both documentary and narrative primary sources. These Ottoman and Muscovite sources show the contrasting subject- and territory-making strategies in the early modern period. They also show how their rivalry brought about changes to the internal dynamics and strategies of the polities within the North Caucasus, shaping the region, its political structures and the lives of its peoples in the following centuries.