This essay examines the level of protection that North American justices have attributed to issues of privacy surrounding personal e-mail. The author takes a close look at the relevant jurisprudence from both Canadian and American Courts, while concentrating his efforts on analysing an employee’s right to privacy and an employer’s right to access personal email received on company terminals. While Canadian Courts try to fill the legislative void by underlining the differences and similarities between emails and more traditional means of communication that have already been subject to legislative control (i.e. the telephone and regular mail), American justices have taken a constitutional approach to the question in adapting their interpretation of the 4th amendment to the U.S. Constitution to this relatively new technology. They have also relied on the Electronic Communications Privacy Act of 1986, and the Privacy Protection Act of 1986, to establish the legal status of emails. Unfortunately, the author concludes that these efforts are not sufficient, for the actual legislation does not consider the true essence of emails.