In the 19th century, American protestant missionaries working in the Ottoman Empire established the oldest lasting institutional connections between the US and the Islamic world. The missionaries’ religious, racial and civilizational arrogance foreshadowed and prefigured later American traditions of Orientalism and exceptionalism. The schools and universities they founded facilitated later paternalistic and imperial American projects in the region. They presented themselves as the human family’s oldest and wisest siblings, setting out to enlighten their benighted brethren overseas. The mission’s most important polemicist, Henry Harris Jessup, wrote that ““Intellectually, the land was in utter stagnation… it was in general true that there were in the land neither books, readers, nor schools, as such… The Oriental mind seemed asleep.” He and his colleagues, he implied, would awaken it. However, the missionaries spent a great deal of time learning at the feet of those who they claimed to be irreparably ignorant. This paper explores how these American missionaries learned to speak Arabic, and how the process of learning changed them. The work of crossing this language barrier was longer and more arduous than their sea voyages, and it forced them into close relationships with native speakers whose goals and beliefs sharply differed from their own. Spending hours each day drilling under the tutelage and discipline of cash-strapped Muslim scholars and former feudal administrators, and further honing their skills by reading classical poetry, histories, and treatises on rhetoric, they adopted a local set of hegemonic ideas about how Arabic should be read and written that valorized the classical language of the Qur'an, a tongue as different from 19th century Syria's spoken vernacular as Latin is from Italian, and as closely tied to Sunni Islam as Latin was to Roman Catholicism. This learning led them into paradox. They created a “vernacular” Bible in a classical, ecclesiastical language that most ordinary Syrians couldn’t understand, and fostered a system of purportedly transformative common schools with curricula little different from the Ottoman Empire’s traditional Islamic maktabs. The story of American missionaries’ language-learning shows us how the first Americans working in the Middle East found themselves remade by the society they wanted to remake, and raises questions about how language-learning practices shape present-day scholars of the Middle East.