Despite the popularity of online course and degree offerings in higher education, a lack of data persists on the unique challenges and opportunities online faculty face. Gaining insights about these experiences is important to ensure the quality of online teaching as colleges and universities continue expanding e-learning programs. Therefore, the purpose of this study is to examine the online teaching experiences of two faculty members through the implementation of reflective study methods. Major findings show that faculty access to professional development and mentoring, isolation and connectedness to the campus community, and academic freedom and curriculum control have significant implications for online teaching and student learning. In the wake of COVID-19 as colleges across the nation suddenly are faced with moving to exclusively online learning, this study is needed more than ever.