This study examines the relationship between one approach to training new online instructors and the ways in which the program influenced their beliefs about and attitudes about teaching online over time. The Technological Pedagogical Content Knowledge (TPACK) model serves as the theoretical framework for analyzing three primarily qualitative sources of data including (1) participants' program application essays, (2) post-training program evaluation data; and (3) a follow-up survey of instructors after they delivered their redesigned course online. Findings reveal that, prior to and immediately following the training, instructors were highly optimistic about their course redesign and skill/knowledge development. After teaching the course online, participants were less optimistic and less satisfied with their training experience than they had been immediately prior to or following the training. Multiple instructors cited a need for additional or continued training and support.