Large zones of de facto political autonomy persist even as various state systems have endeavored to fix, rationalize, and secure external and internal borders. These spaces are products of long histories of uneven extension and exercise of state sovereignty in the subcontinent and much of Asia and Africa. Histories and legacies of borderland autonomy have important implications for contemporary sovereign practice in much of the world. This article examines the making, unmaking, and endurance of borderlands around Hyderabad in the eastern Deccan. It describes the region as an “old borderland,” from premodern frontier zone, to sovereign and autonomous state during the era of British imperial dominance, through its mid-twentieth-century reemergence as a site of state avoidance or resistance. Identifying the productive relationship among frictional environments, political sovereignty, and social and cultural dynamics, this article develops frameworks for historicizing borderland autonomy in South Asia and beyond.