This qualitative, transcendental phenomenological study investigated the possibility that instructors’ perceptions of their roles within Web 2.0 learning environments are not in alignment with the transformative teaching and learning practices that these environments make possible. The aim was to explore the influence of instructors’ perceptions of these emerging environments on their interactions with their students. Seven instructors from a U.S. Air Force academy participated in the study, sitting for long interviews during which they offered their answers to the three research questions:

• RQ1: What do instructors perceive to be their roles in the Web 2.0 learning environment?

• RQ2: What is the influence of instructors’ perceptions on their interactions with students in this environment?

• RQ3: What is the influence of instructors’ lived experiences on their perceptions of their roles in online instruction?

A modified van Kaam methodology served to extract data from the interviews for analysis, eventually generating eight narratives of essence describing instructors’ perceptions of their roles in the Web 2.0 learning environment. An analysis of the narratives using transcendental phenomenology in conjunction with a theoretical framework rooted in transformative learning theory led to the formulation of the following proposition: the emergent definition of educators’ roles and their emergent sense of identity (relating to RQ1, concerning the perceptions of their roles) is shaped by a combination of 2D/3D reconciliation and motivation for change, and the rewiring of sensory inputs (relating to RQ2, concerning educators’ interactions with students) represents a reaction to a gap between expectations and reality and to the difficulties involved in coping with ambiguity and mapping the boundaries of influence (relating to RQ3, concerning educators’ lived experience). Researchers can build on this study by examining larger and more diverse sample populations in future phenomenological studies, by conducting qualitative studies using questionnaires and quantitative ones using surveys, rubrics, and maturation frameworks, by employing other theories and frameworks that support investigations of the phenomena, and by considering multiple disciplines and in particular potential intersections among the functions that these disciplines fulfill.