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This essay proposes Gary Shteyngart's dystopian satire, Super Sad True Love Story, as an appropriate heuristic model for understanding surveillance and society in the twenty-first century. While George Orwell's Nineteen Eighty-Four remains influential, many of his observations now seem anachronistic. Shteyngart, it is argued, offers a more appropriate vision for our world of decentralized digital "surveillant assemblages" that maintain a "control society" with little need for a Big Brother–like state. Unlike Orwell, who predicted the "proles" would be relatively free from surveillance, Shteyngart also emphasizes the disproportionate impact of surveillance on different sections of society. Finally, this essay turns to the thorny question of personal liberty and autonomy as a justification for the right to privacy and as a central theme within the dystopian genre. Many critics argue that dystopian literature is inherently reactionary because of its anti-utopianism and individualism. This essay, however, argues that the kind of autonomy that privacy activists and dystopian novelists most often wish to defend should be understood not as a self-sufficiency but as personhood that is socially embedded and politically engaged, and, crucially, a necessary but insufficient precondition for the resistance and refusal of digital mass surveillance.