Kerry Howley tells the story of Reality Winner, a twenty-five-year-old Air Force veteran and NSA contractor who in 2017 leaked a classified document about Russian election interference and was sentenced to five years in prison. Howley, an essayist and journalist, examines Winner's case as a window into questions of surveillance, secrecy, and what happens when our past selves make decisions our future selves must live with. Winner was a yoga instructor, a gun owner, a linguist who spoke Pashto and Dari, and an idealist who believed the public should know what she had learned. Howley reconstructs Winner's life, her brief career in intelligence, and the swift investigation that caught her. She asks what it means to live in a world where everything we write is potentially evidence, where our digital traces form a record more complete than memory. The book is a character study and a meditation on privacy, conscience, and the carceral state. Howley writes with precision and moral seriousness about a case that illuminates much about contemporary America.