“Liberation” is a common trope in late Ottoman history. It was, and still is, common for narratives to trace the dates at which various polities were freed from the sultan’s rule—usually in the context of international relations, as part of the “Eastern Question.” But at the same time, liberation could be more literal, and individualized, as a growing web of treaties and practice committed the Ottoman state to releasing captives and slaves. This paper puts those two conceptions of “liberation” in conversation, by examining how captors, captives, and the Ottoman state navigated the shifting concept of “autonomy” in the late eighteenth and nineteenth centuries. In doing so, it also explores what it meant to be a “subject” of a patchwork empire, in which different people lived under different legal rules. The paper draws on Ottoman, Russian, and British archival sources, as well as British and French travel narratives. It begins by looking at the original “autonomous” Ottoman territories—Moldavia, Wallachia, and (arguably) Georgia. In the eighteenth century, the inhabitants of all of these territories were bound to Istanbul indirectly. Nevertheless, they could fall prey to enslavement, and over the course of the century, treaties between the Ottomans, Iran, and Russia granted them new rights to demand liberation. Was this a matter of increased autonomy, or evidence of an informal sort of Russian sovereignty extending over them? More importantly, for captives themselves, what type of claims could they make to gain liberation, and what types of legal relationships did this imply? I explore these questions through Islamic court records and imperial decrees from several different Ottoman archives. The second part of the paper turns to the Ottoman state itself. As the Age of Revolutions wore on in the early nineteenth century, the Sublime Porte granted autonomy—and then independence—to more and more territories, most notably Serbia and Greece. This required navigating difficult legal questions about what “autonomy” meant, particularly for people who had been enslaved in those territories during wartime. I approach this question through a detailed look at the liberation of captives after the Greek War of Independence. While previously characterized as the end of “white slavery” in the Ottoman Empire, or as the first step toward abolition in general, I argue that it was instead an attempt to work out the relationship between autonomy and enslavement, and indeed the meaning of autonomy itself.