The fourth amendment to the U.S. Constitution ostensibly protects individuals from unreasonable search and seizure by the State, but says nothing about protection from others, such as supervisors or tabloid reporters who might wish to access your personal information. Moreover, the legal protections that fourth amendment safeguards offer are often circumvented by the State, sometimes legally under judicial review, and frequently illegally. Digital communications, and email messages in particular, are relatively easy to track and monitor without either party's knowledge. Consequently, any reasonable expectation of privacy depends on safeguards implemented by the end users. Many of the people who use digital media to communicate, however, have little to no knowledge of of digital encryption, and few consider their messages sensitive enough to merit such measures. Nonetheless, instances where a reasonable degree of privacy is helpful do arise, from the need to transfer confidential medical or human subjects data to a particularly sensitive personal message. This article briefly addresses the basic privacy issues, and then offers a general introduction to digital privacy protection, including how to implement useful encryption and authentication utilities provided by GnuPG with Mozilla Thunderbird, Microsoft® Outlook ExpressTM, or Microsoft® OutlookTM. Of the different email applications covered, I consider Thunderbird the most well-integrated and straightforward, and I highly recommend it over its commercial competitors. While I typically recommend that most people interested in both secure and flexible computing use a Linux OS, Mozilla Thunderbird and GnuPG both operate on WindowsTM and Mac systems, so you don't need to run Linux to use them. In spite of its advantages, I recognize that many people are more comfortable using proprietary software systems, or their IT departments prevent them from using alternate systems (as mine tried to do once---and only once), so I will do my best to make sure that the tools I describe work with Microsoft® email systems as well.