Building on its predecessor, Queer Tolstoy: A Psychobiography (2023), this book uncovers queer-anarchist dimensions of the second half of Count Lev Nikolaevich Tolstoy's life (1828–1910), and of the Russian writer's later art-works. It features queer-friendly readings of Anna Karenina (1875–1877), The Gospels In Brief (1881), “The Death of Ivan Ilych” (1886), “The Kreutzer Sonata,” (1889), “Master and Man” (1895), and Resurrection (1899), among other classics. However, the argument does not overlook the gross misogyny expressed by Tolstoy in either his art or his marriage with Countess Sofia Andreevna Tolstaya. Rather, the author explores the fundamental contradictions between sexism and anti-authoritarianism, while critiquing Tolstoy's self-defeating commitment to patriarchy. The text also praises the writer's late turn toward preaching Christian anarchism, as it traces aspects of Tolstoy's artistic and political resonance in the twentieth century, including pacifist plant-based communes, the Russian and Mexican Revolutions, the Bloomsbury Group, Catholic Workers, and Soviet-era hippies.