This essay seeks to explain why the United States is struggling to deal with the “soft” cyberoperations that have been so prevalent in recent years: cyberespionage and cybertheft, often followed by strategic publication; information operations and propaganda; and relatively low-level cyber disruptions such as denial-of-service and ransomware attacks. The main explanation for the struggle is that constituent elements of U.S. society—a commitment to free speech, privacy, and the rule of law, innovative technology firms, relatively unregulated markets, and deep digital sophistication—create asymmetric weaknesses that foreign adversaries, especially authoritarian ones, can exploit. We do not claim that the disadvantages of digitalization for the United States outweigh the advantages, but we present reasons for pessimism.