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Hildegund von Schönau has the remarkable reputation of being the most famous of the cross-dressing female saints. Disguised as a boy, she joined the pilgrims journeying to Jerusalem. After returning to Germany, she maintained her male disguise and lived as a male for the rest of her life. Hildegund struggled alone to overcome all of the insecurities of her double life. She “begged and attended the school.” Deemed to be an intelligent young man, she was entrusted to carry a secret letter to the pope in Verona. After successfully completing her mission, she entered the monastery at Schönau under the alias of Joseph. While still in her first year as a novice, she fell ill and died in 1188. Five vitae give a remarkable account of her transgenderism and adventure through the Holy Land and Europe. Medieval cultural and social factors played a very significant role in influencing her decisions about her transsexualism. Hildegund’s biographers repeatedly record her psychological duress in concealing her identity and renouncing her gender. A survey of Hildegund’s life gives the impression that she strongly desired to change her gender and adopt a male role. In modern terms, Hildegund fits into the classification of transgenderism.