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During the early 19th century and the Second Great Awakening, where women were moral custodians in guiding their families towards Christian faith, pioneering female missionaries like Harriet Winthrop Winslow challenged patriarchal norms, transcending traditional domesticity to forge inroads in evangelism and education within the missionary movement. She accompanied her husband to Sri Lanka in 1819, establishing Asia’s first all-girls school in 1823, holistically educating girls and challenging local skepticism and religious customs to advance female education. Analyzing her memoir, which includes her diary entries and correspondence, reveals how she contested prevailing societal and ecclesiastical limitations that placed her subordinate to her husband. Given strict local gender separation, she reinforces the critical participation of women in missionary activities to connect with and evangelize to local women, a task impossible for their male counterparts. Barred from publicly preaching, Harriet instead fostered conversion to Christianity by visiting women in their homes, providing medical care, teaching reading, and mastering the local language; educating locals also became a pathway to disseminate the gospel indirectly. As wives were seen as adjuncts to their husbands and not creators of theology, their missionary efforts have been undervalued. This paper aims to reassess the historical contribution of Winslow within gender, religion, and education in the missionary movement, ultimately fostering a more inclusive understanding of how she empowered females through educational equality and challenged missionary wives’ roles as helpmates.