Like many instructors in higher education, I have found myself increasingly pressed to respond to demands for courses delivered with alternative technologies. This pressure is particularly dramatic today given the expanded access to and use of the Internet (NCES, 1997; NTIA, 1997). Web-based learning environments (WBLEs) are clearly the contemporary instructional “innovation of choice” in higher education. Feeling an obligation to extend my own professional preparation in this area, as well as a desire to determine the real issues associated with learning and teaching on the Web, I have ventured forward with a variety of WBLE experiences. This chapter is a case study description of my rookie experience teaching in an on-line environment that was custom designed to focus on learner and pedagogy issues found in the contemporary literature.