In 2008, a monument to the gay victims of the Holocaust was erected that paid tribute only to its male victims, reigniting a long-running debate regarding the fate of lesbians in the Third Reich. Using four previously unanalyzed police investigation files at the Landesarchiv Berlin, this article opens a window into the lives of lesbians living in Nazi Berlin. The four case studies below highlight the capricious nature of Nazi rule and the surprising ways in which discourses of homosexuality appeared in the everyday lives of prostitutes and factory workers. At the same time, they demonstrate a surprisingly robust and open world in which lesbianism was not only not persecuted, but even tolerated in limited ways. While these materials suggest a chasm that separated the experiences of gay men and lesbians under the Nazi regime, they also highlight not only the limits of tolerance but the ways in which it can reinforce persecution itself.