Electronic mail (e-mail) has become increasingly important in the workplace. The growth of this new medium of communication has generated important legal questions about the privacy and monitoring of e-mail messages, so much so that most experts strongly recommend that organizations adopt explicit policies about e-mail for their own legal protection. The legal questions concerning e-mail in the workplace include both: (a) employee rights to privacy regarding e-mail messages; and (b) employee obligations to monitor e-mail to ensure a suitable workplace or to prevent illegal behavior. We discuss both of these topics in this chapter, attempting not only to outline current legal thinking in the area, but also to raise questions that managers and policy makers should consider. It is worth noting at the start that many of the legal issues surrounding the use of e-mail are direct extensions of principles that apply to other forms of communications. Indeed, much of the law that governs e-mail is not legislation that was written explicitly to cover this particular form of communication. Issues of the privacy of employee e-mail messages, for example, are directly analogous to issues of the privacy of employee phone calls or written correspondence. To be sure, there are questions about exactly how legal principles that were established for older communication technologies should be applied to a new one, and perhaps not all of these questions are fully settled at this point in time, but our understanding of this topic is broadened if we appreciate the application of legal principles across communication media.