In the first decades of the 20th century, hundreds of Syrians moved through and within Oklahoma and Indian Territories, United States, an area that in 1907 became the 46th U.S. state of Oklahoma. This paper describes some ways first- and second-generation Syrian American women negotiated patriarchal family and settler dynamics in Oklahoma at the site of entrepreneurialism. Drawing on private documents, published and unpublished auto/biographies, interviews, periodicals, and secondary sources, the paper chronicles Syrian women within a variety of Oklahoma regional cultures and economies--mining, railroad, cotton, wheat, and oil. It describes how different multi-spatial relational logics vied to enable, O/orient, and/or constrain entrepreneurialism among Syrian women in Oklahoma,yet how these women afforded themselves degrees of independence and agency as peddlers, teachers, lacemakers, midwives, farmers, butchers, Indigenous art dealers, and merchants of a variety of goods, including ready-to-wear Western lines and luxury haute couture for regional oil elites. The paper emphasizes Suad Joseph's description of connective patriarchy as a dynamic construct of belonging and ideals not discrete from political economy--in the case of Oklahoma, Indigenous dispossession, extractivism, and emerging petrocultures.