Most scholars, medieval as well as modern, have understood dhimmi status as a legal arrangement in which non-Muslims under Islamic rule abided by a series of discriminatory restrictions and paid jizya, in return for which they secured their property from plunder and their persons from being enslaved or killed. Yet the post-Mongol Türkmen beys, amirs, and sultans who ruled from Anatolia to Central Asia did not feel bound by such restrictions on their revenue-capturing activities. Plundering the sedentary population, even sometimes the Muslims, is abundantly attested in historical sources from the period, as well as captivity. Some captivities were brief, ending upon payment of an agreed-upon ransom, while other captivities were more open-ended and sometimes involved long-distance relocation. This paper considers the forms of captivity, and the evidence that sometimes enduring captivity took the form of enslavement, in light of recent scholarly discussions of varieties of unfreedom. Sources for the study include descriptive texts in an array of languages and genres (Armenian colophons, Persian court histories of Timur and of Uzun Hasan Aqqoyunlu, and Syriac chronicles continuing the tradition of Ibn al-Ibri), as well as the normative discussions of dhimmi status and enslavement (istirqaq) found in works of Hanafi fiqh, the madhhab which claimed the loyalty of Türkmen rulers. These sources allow us to show that, while juristic sources distinguish precisely between captivity and enslavement, or between ransom and sale, the social processes involved were more continuous. The distinction between “the law on the books” and “the law on the ground” is familiar from socio-legal history in other fields, but historians’ awareness of Islamic social history has often been hindered rather than helped by the influence of normative texts on narrative accounts, whether medieval Arabic sources or modern scholarship. The example of enslavement of dhimmis illustrates how the notion of a unified dar al-Islam run according to “Islamic law” developed by the ulama was an illusory fiction, useful to the ulama’s attempts to bolster their own social power and prestige, when in reality the multitudinous rulers of the region created their own rules subject to the practical limitations of governing diverse populations.