In the United States the words “telephone surveillance” bring to mind contemporary security concerns about smart phone tracking, the NSA warrantless wiretapping scandal, and the telecommunications provisions of the Patriot Act. Yet telephone surveillance is as old as telephony itself, dating back to the nearly simultaneous commercialization of the telephone and phonograph. This article examines telephone surveillance by American law enforcement agencies from the inception of telephone service to the passage of the Federal Wiretap Law in 1968, focusing on the challenges an advancing, proliferating, and shrinking technology posed for Fourth Amendment law. To highlight the technological, institutional, and cultural interactions that have shaped Fourth Amendment jurisprudence, the article deploys Jack Balkin’s theory of cultural software and Anslem Strauss’s concept of a negotiated order and brings together major cases, federal legislation, and evidence of government surveillance. The article argues that during the first ninety years of telephone usage in America, laws on search and seizure developed not from constitutional consistency or logic but as the result of a complex negotiation process involving new media and human agency.