Though most people recognize John Van Ess as the most influential missionary in Iraq during the World War era, Dorothy Van Ess a less flamboyant character, was the force behind the American missionary schools of High Hope and family consumer clubs for girls in Basra-Iraq from 1912-1955. Nevertheless, her contribution in education and in outreach methods was always overshadowed by her husband’s seniority. Despite the effectiveness of the missionary woman’s outreach methods in Basra not much credit was given to them in the historiography. The Van Esses’ position as language and culture experts during the great political transformation in Iraq enabled the couple to participate in imperial negotiations between local power brokers and the British occupation authority. Even in a male dominated society, Dorothy managed to gain the trust and the attention of power brokers in the region. She may be the only woman besides Ms. Bell to witness the important talks between the paramount sheikhs of the region and the British to determine present and future alliances. Take into account, Dorothy’s personal journals, letters, and her well-known publications for the Arabian Mission, this paper evaluates Dorothy’s methods of outreach and her access to women’s household in and around Basra. It demonstrates how she recruited her students, gained favors among influential families, and became associated with powerful British authorities in the region like Ms. Bell. This paper defines Dorothy’s role not just as a facilitator of her husband’s work but as a main player in the success of the schools, including her husband’s school for boys.