This dissertation argues that gender is an important tool of analysis in understanding Jewish conversion to Christianity in the High Middle Ages. It establishes that Christian sources describe Jewish women as malleable and easy to convert, with their male counterparts appearing as stubborn and in some cases hostile towards Christianity. Meanwhile, Jewish sources describe women as stalwarts of the faith, who are more willing to give up their own lives rather than convert to Christianity, and are willing to do so much more frequently than men. I argue that Christian sources are influenced by medieval ideas about gender, which included the idea that women were naturally more malleable than men. Meanwhile, Jewish sources, in response to the massacres and forced conversions that occurred in the Rhineland in 1096, attempted to portray a unified front of resistance to Christian influence, and this included elevating women to their status as the “corner pillars” of Judaism. Jewish sources minimize any record of Jewish conversion to Christianity, while Christian sources feature many prominent female converts, making it difficult to know whether Jewish men or women converted more regularly. Through an examination of both Latin and Hebrew administrative documents relating to conversion that feature the cases of 308 individual converts, I found that around 40% of converts to Christianity were female