Objectives: The purpose of the study was to examine narratives about the effect of the sudden transition from face-to-face teaching to emergency remote teaching necessitated by the COVID-19 pandemic on postsecondary educators. Method: We conducted interviews with 11 post-secondary educators from five post-secondary institutes in one province in Canada. Educators were asked to reflect on their experiences during the transition from in-person to remote teaching and learning. Results: Our thematic analysis revealed that educators' experiences were influenced by three main factors: (a) student engagement, interactions, and persistence in learning; (b) competence in the application of teacher technological pedagogical content knowledge (TPACK); and (c) overall well being of faculty and students. Conclusions: Participants had unique experiences, and institutions varied in the ways they supported students and staff. Those educators who had expertise, experience, or professional support in technology and teaching seemed to have an easier transition. Implication for Theory and Practice: Higher education institutes should support educators in enhancing their technological pedagogical knowledge and in facilitating learning in various delivery modalities.