Population growth (Broad, 1997), institutional competition (Daniel & Cox, 2002), and changing learner needs (Willis, Tucker, & Gunn, 2003) are among the issues influencing the increase in online teaching and learning. Related to this, emergent and expanding distance learning technologies have subsequently pitted "brick and mortar" against "online" paradigms. This has resulted in a need for research to clarify the relevance, effectiveness, restrictive and facilitative dimensions of online courses. For example, faculty are increasingly expected and encouraged to develop and teach online courses often with misperceptions about required pedagogical skills and without adequate support and preparation (Choi & Park, 2006). This qualitative study is therefore, aimed at sharing the experiences and perspectives of two novice online instructors' operating within two colleges in the eastern US. These instructors initially shared that a key motivation for the teaching of their online courses was fear of becoming professionally out of date and of "giving in" to technophobia. This paper reports on the background to--and different approaches adopted towards--developing two online courses as well as providing student perceptions of their on-line learning experience. Findings and recommendations from this research are aimed at providing an insight into some of the fundamental issues that other novice "online" instructors will need to consider in developing their own technology mediated courses.