The United States of America entered World War I in 1917, but it never formally declared war on the Ottoman Empire. Nevertheless, President Wilson’s mass mobilization for the Selective Service draft prompted the legal reclassification of a quarter million Ottoman subjects living in the United States as “enemy aliens,” a complex status that prohibited them from military service and made them subject to heightened public suspicion. Government concerns about the movements, commerce, and nationality status of Ottoman immigrant nationals produced new obstacles for the large Syrian and Lebanese communities in particular. And in the context of the War, American nativists accused Syrian immigrants (who were exempt from the draft) of being “alien slackers,” and of capitalizing on the U.S. government’s hesitance to employ them militarily. At this critical juncture, questions about 1) Syrian Americans’ eligibility for military service and 2) Syrian immigrants’ potential for U.S. naturalization and citizenship merged. As a result, immigrant activists promoted military service as the best possible means towards obtaining American citizenship and shedding their Ottoman nationality. This paper assesses a series of campaigns by immigrant political societies to enlist Syrian Americans into the U.S. Army as a means of obtaining U.S. citizenship. Using the records of Syrian immigrant fraternal societies in New York City and Boston, the paper argues that immigrant leaders developed clandestine networks of recruitment, funneling Syrian Ottoman nationals from across the Americas into the military and participating in a quasi-legal trade in American visas and passport documents in the meantime. During the War, Syrian immigrants stood upon a fraught legal frontier between Wilson’s America and the Ottoman Empire. The ambiguities concerning the nationality, naturalization, and mobilization of Syrian immigrants created new fissures within the community, fracturing Ottoman loyalists from Syrian, Lebanese, and Arab nationalists in ways that influenced this diaspora’s politics for years to come.