Freire’s notion of dialogical pedagogy, where the student and teacher mutually grow and learn together and provide opportunities for personal and social gains, assumes the development of deep and meaningful dialogue in the learning environment. The virtual learning environment poses an interesting challenge to this notion, whereby dialogue is constrained by time lags in communication over discussion forums, blogs and even over email. Successful online courses must, therefore, go beyond technological changes only, and require teachers to commit to pedagogical changes while transitioning from a classroom environment to an online environment. By gathering qualitative data from educators who have recently transitioned from face-to-face to online teaching at New Zealand tertiary providers of education, this study develops an understanding of how online educators pick cues from the discussion platforms offered by virtual learning environments to critically reflect on their pedagogical practice, and the associated changes they make to help students achieve their learning outcomes. It critically assesses how dialogic pedagogy and critical reflection can be adapted to fit in the framework of virtual learning, and contrasts these philosophical ideas to the Western criticism of automation and de-professionalisation of universities in the wake of increased distance learning options provided by tertiary institutes. The findings have been discussed within a post-intentional phenomenological framework, which focuses on what structure the phenomenon might take rather than what it already has. The findings from this dynamic inquiry will help online educators develop deeper understanding of the ever-changing nature of social, ethical and political relations in an online context. The philosophical underpinnings of this research assume critical reflection, as popularised by John Dewey, and dialogical pedagogy, developed by Paulo Freire, to be compatible concepts. Developing critically meaningful relationships with students, through dialogue, complements critically reflective practice. A healthy dialogue between the teacher and students, where each is encouraged to actively engage in discussions and amend or revise their views about various aspects, can make the process of reflection more productive. The virtual learning environment does not offer the same promptness and flexibility that is there in the conventional, face to face context. Developing this personalised relationship with students, and limited space for conventional dialogue, can act as a challenge for online educators to critically reflect and make relevant pedagogic adjustments. The findings from this study reveal that the prior teaching experience of educators in a face-to-face environment can help them in critically reflecting on their pedagogy as they move towards an online teaching and learning environment. With students shying away from engaging in dialogue in the online environment, educators resort to finding alternate ways to keep students engaged with the online tasks. The motivation of the education institution for transitioning to the online environment, and whether they keep the educator’s feedback on-board as they make this transition, also determines how ‘present’ and actively engaged educators themselves will be in the online learning environment.