Amid economic crises, rising totalitarianisms, and escalating technological warfare of the 1930s and 1940s, Bloomsbury’s thinkers and artists entered a new phase. They had never thought alike, nor considered themselves a “group,” but, beyond their colorful private sociability, these public-spirited “civilized individuals” carried the banner of their liberal intellectual formation – their critical hope and utopian idealism – into collective arenas. Drawing upon the late art, thought, letters, and conversation of Sigmund Freud, John Maynard Keynes, E. M. Forster, T. S. Eliot, Virginia Woolf, Leonard Woolf, and Vita Sackville-West, this chapter explores late Bloomsbury’s dialectic of enlightenment, as darkening skies tested the hope that European civilization, smashed by the Great War, might be rebuilt on firmer and more lasting ground. As domestic and international crises bore a shrinking world toward an unknowable future, Bloomsbury’s civilized individualism – which, Raymond Williams thought, offered no vision of a whole society – springs into high relief against the existential threat of totalitarian systems on right and left that emerged from radically different national histories. In late Bloomsbury, we glimpse the threats of authoritarianism, racialized imperialism, genocidal violence, all-consuming capitalism, and earth-ravaging technological modernity.