The Problem with Personalization examines the historical development and contemporary consequences of personalized advertising. Joseph Turow traces efforts to tailor commercial messages from early forms of individualized selling through mass media, direct marketing, digital tracking, predictive analytics, and generative artificial intelligence. The book explains how advertisers, technology companies, retailers, and media organizations collect and analyze consumer data to create increasingly individualized messages and experiences. It also considers the implications of these practices for privacy, autonomy, public discourse, and shared social experience. Drawing on historical research, industry interviews, and analysis of emerging technologies, Turow argues that modern personalization extends longstanding advertising ambitions while greatly increasing their scale and precision. Written for readers interested in marketing, media studies, technology, and public policy, the work provides both a history of targeted advertising and a critical assessment of its social consequences