Every Fourth Amendment analysis begins with the threshold inquiry of whether there has been a search or seizure. But answering what constitutes a “search” for the purposes of the Amendment has shown to be a difficult task. This is especially so in a world that is constantly changing by way of technology. Since the Amendment was written, both the capabilities of law enforcement as well as the private and commercial use of information have drastically transformed. For that reason, the doctrine has evolved substantially. Search criterion has shifted from physical trespass to reasonable expectations of privacy. Further, no such expectation exists in information that one knowingly reveals to a third party. But, in the Digital Age, these principles suffer from lack of clarity. Carpenter v. United States was the most recent confluence of the Fourth Amendment and technology, wherein the Supreme Court held that a search occurs when the Government obtains a user’s cell site location information. This note analyzes that case, as well as historic and contemporary search doctrine. Ultimately, this Note argues that search questions—even those implicating technology—are best answered by applying the Amendment as written.