This dissertation argues that “disaffection” is an overlooked but foundational posture of mid-twentieth-century British and Anglophone literature. Previously misdiagnosed as quietism or apathy, disaffection instead describes how many late modernist writers mediated between their ideological misgivings and the pressure to respond to dire political crises, from the Second World War to the creation of new postcolonial nations. Stylists of disaffection—such as Henry Green, Virginia Woolf, Elizabeth Bowen, and V. S. Naipaul—grappled with how limiting cultural assumptions, for instance, about class and nation, seemed to inhere in particular aesthetic techniques like stream of consciousness or realism. Disaffected literature appeals to but then disrupts a given technique’s projection of these assumptions and the social totality that they imagine. This literary “bait-and-switch” creates a feeling of dysphoria whereby readers experience a text unnervingly different from what they had been led to expect. Recognizing the formative work of literary disaffection in late modernism offers an original way to conceptualize the transition between modernist and postmodernist literature in the twentieth century.