Modern technology records unprecedented amounts of data about individuals, and developments in surveillance technologies have removed many practical limitations on government collection of this information. A Fourth Amendment test called the third party doctrine permits the U.S. government to collect vast amounts of this electronically-stored data without any individualized suspicion. This thesis explores how the failure to create legal barriers preventing indiscriminate data collection chills citizens' First Amendment rights. Courts, legal scholars and social scientists have documented how pervasive surveillance restricts free expression and even free thought. This thesis endorses a technology-centered approach to the Fourth Amendment, which asks whether government's method of collection has the capacity to facilitate broad, indiscriminate surveillance. This approach better protects free expression and reasonable expectations of privacy by focusing directly on the fundamental challenge facing modern Fourth Amendment jurisprudence: the current practical and constitutional feasibility of mass surveillance methods that chill First Amendment rights.