This qualitative study examines expert instructors’ lived experienced with online pedagogy in order to (1) understand how teaching in a virtual environment influences pedagogical style, academic identity and student-instructor interactions and (2) to explore how the virtual teaching experience evolves as faculty continue to teach online. None of the existing empirical research has focused on accomplished instructors’ online teaching experiences and, as a result, there is very little information concerning how to sustain faculty approval, retain skilled instructors, provide adequate online teaching support and maintain a successful online learning enterprise over time (Coppola, et al., 2002; Bolliger & Wasilik, 2009; Betts, 2014). Using a constructivist design, this study employed interviews and content analysis techniques to explore the following research questions: 1) What challenges do experienced online faculty face when they teach in the virtual learning environment? 2) What new challenges have emerged as a result of their continued online teaching experience? 3) How do experienced instructors approach and address these challenges? Thirty-one self-identified experienced online instructors from across the nation and a variety of institutions participated. Findings show that continued online teaching experience has a profound impact on the way instructors perceive their pedagogical practice, their place in the academy and their role in students’ online learning experiences. The online environment presents instructors with a multitude of challenges. These challenges are complex and involve pedagogical issues as well as philosophical dilemmas that force instructors to reconsider their assumptions about teaching, learning and authority in the classroom. Wrestling with these issues puts instructors in a vulnerable position as they search for pragmatic solutions and simultaneously renegotiate their long-held academic assumptions and beliefs. The practical and philosophical challenges instructors experience in regards to their developing digital pedagogical practice, their changing relationship with students, and their evolving online academic identity are discussed as well as findings related to vulnerability in the online environment. Implications for online faculty development, limitations and areas for improvement are also considered.