Drawing from a wide range of archival materials from the late Ottoman Empire, including slave petitions, slaveholding elites’ correspondences, police interrogations and court records, this paper focuses on the complex intersection of three major developments in the late Ottoman Empire: 1) the Ottoman Reform Edict in 1856 and the subsequent legal reforms, 2) the trade ban in African slaves in 1857 and its transforming effects on the Islamic law, and 3) the Caucasian expulsion in early 1860s and the transplanted customary law in the Caucasian settlements across the Ottoman Empire. Firstly, it traces how legal practices were carried over with Caucasian refugees to the Ottoman domains and how different legal systems interplayed with and worked against each other in determining not only the limits of slavery, but also how such liberal “fictions” as freedom and the equality before the law were vernacularized by the local agents in the Ottoman Empire. It navigates within a set of legal records, specifically of those that were called “freedom suits” (hürriyet davaları), with the aim of exploring how slaves built their claims in relation to different legal terrains, problems and concepts. Secondly, it looks at how legal institutions transformed during this time. Beginning with the foundation with the Supreme Council for Judicial Ordinances and especially after its transformation into the Ministry of Justice, the divide between the Ministry and the Office of the Shaykh al-Islām (which oversaw the Sharia courts in the country) became steep. Instead of looking at them as two separate bodies however, one that was aggressively taking over the entire legal practice and the other increasingly more confined to the domestic sphere, this paper uses slavery to examine the ways in which they cut across each other. Lastly, it briefly canvasses how these processes also bent the categories of ethnicity, race and gender, and speculates on the ways in which they added to the “violent turn” of events in the subsequent decades.