Reading May Sinclair’s A Journal of Impressions in Belgium, Radclyffe Hall’s The Well of Loneliness and “Miss Ogilvy Finds Herself,” and Helen Zenna Smith’s (pen name of Evadne Price) Not So Quiet . . . Stepdaughters of War, I argue that May Sinclair, Stephen Gordon, Miss Ogilvy, and Helen Zenna Smith, the main characters of these texts, do not achieve the female empowerment and liberation that many scholars of WWI women’s ambulance service, especially Sandra M. Gilbert and Susan Gubar, describe. Instead, the benefits of these characters’ ambulance service are more personal yet bittersweet. In chapter one, I argue that May Sinclair uses her time with the Munro Ambulance Corps as a form of ergotherapy and her memoir about that time, A Journal of Impressions in Belgium, as a form of talk therapy, treating the hysteria or neurasthenia that a patriarchal society causes in women. However, Hector Munro, the Commandant, dismisses Sinclair after only seventeen days. In chapter two, I argue that The Well of Loneliness is not a lesbian novel but a trans narrative, so Stephen Gordon is using her novels and ambulance service to advocate for transgender acceptance. When Stephen begins to doubt her ability to achieve this goal, though, she ends her longtime relationship with Mary Llewellyn, whom she drove ambulances with at the front. Likewise, I argue that “Miss Ogilvy Finds Herself” is also a trans narrative: when Miss Ogilvy founds and leads an ambulance unit in France, she finally fulfills her lifelong wish to be a man, but when the unit is disbanded after the war, Miss Ogilvy is distraught and takes a vacation to ease her nerves. There, she has a long, happy dream about being a man, but never wakes up. In the third chapter, I argue the Helen Zenna Smith is a closeted lesbian. At first, she is filled with self-loathing, helping torment other lesbians in her ambulance unit, but as she realizes and accepts her orientation, she begins to pursue other women in the unit, only for the war to take them one by one, devastating Smith.