Under current doctrines, parties to a communication enjoy robust constitutional protection against government surveillance only when they have a reasonable expectation of privacy in those communications. This paper suggests that the surprising dearth of case law applying the reasonable expectations of privacy test to modern electronic communications reflects courts' discomfort with the test's necessarily normative analysis. That discomfort also likely explains courts' use of shortcuts based on Miller v. United States and Smith v. Maryland in those few cases that have considered online surveillance practices. In particular, the government has argued that a broad third party rule deprives electronic mail of Fourth Amendment protection merely because Internet Service Providers (ISPs) may access those e-mails. Similarly, some courts have denied Fourth Amendment protection to information stored on computer systems other than e-mail contents, by over reading Smith to provide a bright line at contents/non-contents. Both analytical shortcuts not only miss the point of the Katz v. United States, which established the reasonable expectations of privacy test, but also dramatically under protect privacy, with pernicious results. This paper articulates a first principles approach to constitutional protection that focuses instead on the reasons electronic surveillance requires significant judicial oversight. In particular, it argues that electronic surveillance that is intrusive, continuous, indiscriminate, and hidden should be subject to the heightened procedural requirements imposed on government wiretappers. Because surveillance of stored e-mail, such as the type at issue in the case of Warshak v. United States, often shares the characteristics of this four factor test, it should be subject to the highest level of constitutional regulation.