TABLE OF CONTENTS

Finn Brunton

Screenshot of log-in page for Ashley Madison, October 15, 2015.

THE STORY of the 2015 hack of the adulterous-hookup dating site Ashley Madison starts with a party in Manchester, UK, in 1950. It’s a hypothetical fete, imagined by the great mathematician, computing pioneer, and cryptanalyst Alan Turing, at which a game is played: You, the “interrogator,” are sitting at a teletype keyboard or something like it, chatting with a man (X) and a woman (Y). They’re both trying to convince you that they’re female; the object of the game is for you to guess correctly who really is. You ask: “Will X please tell me the length of his or her hair?” The man tries to pass as the woman; the woman tries to expose him. Turing’s twist on this game is famously known as the Turing Test: “We now ask the question, ‘What will happen when a machine takes the part of [X] in this game?’” This replaces the philosophical quandary “Can computers think?” with “Can computers

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