U.S. citizens are in a constant battle for their rights to privacy, fighting the government’s increasingly pervasive surveillance and justicial needs. One area where court opinions conflict with the public’s expectation of privacy is over the realm of personal electronic communications. The general public believes electronic communications must be afforded a certain level of privacy that is not currently recognized by case law or statutes.  Under current case law, warrantless searches and seizures of your personal e-mail are not prohibited by the Fourth Amendment. 
Fueling the public’s disconnect is the fact that technology progresses faster than the law.  The Constitutional Framers did not consider the depth and variety of technology used daily by every individual, nor did they predict the repercussions their words would have upon new technological uses.  Congress did not anticipate the widespread, various uses of electronic communications when they drafted much of the applicable legislation.  Furthermore, most courts rely upon legal reasoning that only tenuously analogizes between traditional methods of communication or privacy protections in light modern electronic communications. 
Based upon this legal backdrop, courts generally refuse to recognize society’s expectation of privacy over electronic communications.  Courts still hold onto outdated legal analyses for outdated technologies–and apply them as best they can to the burgeoning world of new technologies.  As a result citizens must turn to extralegal protections, such as implementing various technologies to circumvent legal prescriptions. Individuals must work with these new technologies to protect their Fourth Amendment rights.
The classic two-prong test in judging whether the Fourth Amendment protects an individual’s right to privacy asks: (1) whether the individual expects privacy, and then (2) whether society finds this expectation reasonable.  The first prong, the subjective expectation of privacy, is difficult to contest because a defendant will almost invariably affirm that expectation.  Therefore, the second prong is what courts generally focus upon.  Yet it is this second prong that most often flies in the face of what the general public accepts–that courts’ interpretations of the Constitution do not reflect the subjective expectations of society.
Thus, where case law and statutory reforms have continually narrowed privacy protections over electronic communications, the citizenry’s only option is to demonstrate to the courts and the legislature how they wish their rights to be preserved.  Until then, this paradox of perceived privacy rights drives individuals to implement extralegal technical methods such as encryption and anonymization to protect what they perceive to be theirs by right. Whether the courts and legislature follow these trends is an issue that needs to be decided sooner rather than later. 
For the purposes of this article, electronic communications will be narrowly limited to electronic mail (“e-mail”) and in some cases also instant messaging communications (“IM”) or similar “one to few” messaging systems. American Jurisprudence defines electronic communications as “the exchange of ideas, messages, or information, by written word, and includes information communicated to or received by an individual and information communicated concerning an individual’s Internet usage.”  Practically speaking, this includes, at the least, e-mail, web-browsing histories, instant messenger communications, participation in synchronous “chat rooms” or asynchronous “bulletin board” messaging systems (“bulletin boards”), “buddy lists,” and address books. The scope of this accepted definition is too broad for the purposes of this article. In many cases, the technology and implementation may be sufficiently similar to merely extend the legal reasoning here to understand the protections afforded them.
B. Framing Hypothetical: You and Your Eco-Terrorist Friend
Consider a hypothetical: You are an environmental rights activist. One of your colleagues is a suspected eco-terrorist. Now your electronic communications are under investigation in connection with local eco-terrorist activities. Whether or not you are in communication with this suspected eco-terrorist, are your e-mails protected from warrantless search and seizure? If not, then what can you do to protect your own expected right to privacy over your e-mail?
The Fourth Amendment should be your source for protecting your e-mails when you are under scrutiny as a private citizen in a public cyberspace. Regardless of whether you have anything potentially illegal in your e-mail, you suspect that you have the right to be notified by a warrant of any search of your e-mail. A warrantless search of your e-mail, revealing private thoughts and details to strangers, may open you up to the type of indignity similar to that prohibited in Terry v. Ohio.  Yet, courts have refused to grant the contents of e-mail this Constitutional protection.
The remainder of this article will examine the case law and statutes controlling this situation and examine technological implementations that may protect your expectation of privacy in light of your exposure to the eyes of the government. It will then explore this lack of privacy as the type of panoptical society described by the philosophers Jeremy Bentham and Michel Foucault. Finally, it will close with a discussion of methods of “panoptical prophylaxis”–what extralegal technologies are available to individuals interested in protecting their privacy? Also, this article will discuss the issues of privacy and communications in virtual world environments and their effects on “real world” privacy expectations and protections.