This paper studies eleventh- and twelfth-century merchant letters alongside contemporary Arabic chronicles and hisba (market-inspector) manuals in order to demonstrate how a variety of actors managed the logistics of the slave trade to Cairo from sub-Saharan Africa and regions of the western Indian Ocean. Merchants’ correspondence shows how individual buyers turned to their business and personal networks in order to secure domestic slaves and organize the slaves’ transport over long distances. Such documentary evidence suggests that it was far more common for most domestic slaves to be shipped individually as one commodity, or in small numbers, among a mix of goods. When we juxtapose the trade described in documentary sources with the accounts of slave shipments found in chronicles, it becomes clear that the slave trade in the medieval Islamic World was multi-stranded. Chronicles tend to focus on a strand of the slave trade comprised of prestige gifts—that is, diplomatic exchanges between heads-of-state that included slaves. Such prestige gifts reflect highly specific historical contexts and diplomatic practices. Yet most scholarship on the slave trade in the medieval Near East generally, and in the eleventh- and twelfth-century Middle East specifically, has understood such high profile slave exchanges as representative of larger patterns and trends. By focusing on little used documentary sources, we gain a ground-up view of the slave trade that suggests a very different picture of how merchants managed this activity on a daily basis. The smaller scale and more diffused organization of this more quotidian trade encourages scholars to question our own assumptions about what kind of slave trade we have gone looking for in our various sources. This paper will suggest that our understanding of the medieval slave trade in the Islamic World has been unduly shaped by a preoccupation with forms of slave trading that resemble practices more common to the early modern Atlantic and Indian Ocean trades. While Jewish merchant letters from the Cairo Geniza will form the primary basis of this study, letters of Muslim merchants in the Red Sea port of Quseir suggest a similar pattern of slave trading.