This article presents findings from a case study related to the risks associated with the choice of traditional, tenure track faculty to teach online. Education offered at a distance via the World Wide Web is on the rise; so too is the demand for university faculty members who will teach those courses. While traditional academic and professional expectations remain unchanged, the new medium presents a new context in which these faculty members live, work, and balance personal and professional decisions. This study provided a multi-dimensional perspective on one college of education's faculty and administrators as they seek to negotiate this emerging environment. Interviews with faculty, administrators, and faculty peer reviewers were conducted to provide a more complete, triangulated picture of the case.