Three Syrian women who immigrated to the United States in the nineteenth century broke the mold: they were non-normative in almost every facet of their lives, in no way conforming to society’s expectations of Victorian or Syrian womanhood. They had unconventional marriages, determined their own careers, made and kept their fortunes, and controlled not only their own lives but those of their relations. They were spectacularly successful. Marie Azeez, Sophie Daoud, and Selma Gobreen earned the (perhaps grudging) respect of their fellow immigrants as well as Americans, to whom they became well known. Most Syrian women who immigrated in the nineteenth century immediately went out to work; the precariousness of the diasporic economy demanded it. Like the men, they mainly became peddlers. Traveling alone, in pairs, or with male relatives they sold small goods from the “Holy Land” like rosaries or olive-wood boxes, cheap jewelry, notions, and household items, or specialized in fancy goods like laces, embroideries, or “Turkish goods.” Factory work, which was one of the only other jobs open to them, was much less lucrative, so most chose peddling. Women peddlers sold mainly to women, yet despite this, Syrian and American men saw peddling by women as shameful: they were exposed to unsavory people, slept in the rough, and worked unsupervised. Peddling was physically and morally risky. Just earning their own living called into question their honor and therefore that of their male relatives. In addition to attracting censure, the work was arduous, could be dangerous, and did take women far from home, so they generally stopped peddling when they married and either stayed at home or set up a mom-and-pop shop with their husband, finally conforming to the gender expectations of nineteenth-century society. For numerous and obvious reasons, there are few contemporaneous sources for Syrian women of the first wave of immigration, but the three women described in this paper were noticed, written about, and managed fortunes, all of which generated documents. By interrogating these sources, this paper will describe women who were able to defy expectations—both by choice and circumstance—and who were thereby able to accomplish what others could not. They reached a level of independence thought to be reserved for men and set an example of the possibilities open to those who were willing to risk censure in pursuit of independence.