Ephraim Moses Lilien (1874-1925) was one of the most important Jewish artists of modern times. As a successful illustrator, photographer, painter, and printer, he became known as the ‘first major Zionist’ artist. Most of the reception and commentary on Lilien’s images has concentrated on the gendered discourse surrounding his construction and imaging of the ‘New [male] Jew’ as athletic, heroic, and explicitly heterosexual. In this proposed paper, I summarise my research findings from my recently republished monograph for Bloomsbury Press (Gender, Orientalism and the Jewish Nation, 2021), and consider how radical Lilien’s complex depictions of women were for this period. There has been little debate on his images of the modern Jewess. Like other vanguard male artists at the end of the nineteenth century, painting continued to be a male preserve. His work mirrored the misogyny inherent amongst non-Jewish avant-garde artists. Ironically, as a secular Zionist, Lilien pushed the limits of Jewish visual representation in the interests of Jewish cultural literacy. This paper considers that paradox in regard to the burgeoning interest at the fin de siècle in German Orientalism, the place of gender in emerging nationalist agendas and the tensions and difficulties inherent in the navigation of German-Jewish identity. Lilien`s female images offer a compelling glimpse of an alternate, independent and often sexually liberated modern Jewish woman.