The COVID-19 pandemic has shifted the contextual matters of education at all levels, for example, geographic location, community engagement in education and socioeconomic factors, to mention some contextual matters. Awareness of these matters stimulates critical reflections on the depth of preservice teachers’ pedagogical content and pedagogical knowledge. This paper examines preservice teachers’ pedagogical mobility in periods that rely on disruptive innovation. Preservice teachers’ placement settings changed rapidly because of COVID-19 regulations which impacted face-to-face and online teaching and learning environments. This investigation focused on professional learning under the ambit of teacher education, which up to now has been focused on face-to-face teaching pedagogies. The rapidly changing context has made the classroom the pedagogical anchor of education theory and practice. Using a reflective case study approach, we investigated (a) preservice teachers’ pedagogical challenges, (b) the meaning of pedagogical flexibility and innovative pedagogical mobility, and (c) the application of teacher performance and teaching standards in a teaching and learning environment affected by COVID-19. The critical self-reflective narratives offer insight into lived experiences and multiple contextual challenges that raise questions about well-prepared preservice teachers.