The deep disruption to education caused by the move to online learning during COVID-19 was unprecedented. While most educational stakeholders adapt to the transition back to a "new normal", it seems an obvious time for constructivist reflection on the lessons learned. The aim of this longitudinal inquiry was to examine the experiences of higher education learners in Chile during the pandemic for potential insights to be gained. The focus was on students in multidisciplinarian fields and the changes to their perspectives, practices, and identities. Working within the qualitative paradigm, data was gathered using interviews (n=22), surveys (n=1,054, n=1,137, n=205) and field notes. Learners' experiences were mapped against contemporary e-learning theory and 21st century learner identity goals. Through this lens, pedagogical practices, course designs, and uses of technology reflected in online spaces were found to influence learners and their learning in complex ways. Two key themes emerged in the analysis: (1) exposure to conventional pedagogy, information transfer and assessment-driven designs and technology challenges online, left students discouraged with their learning progress and disparaging of their future workplace preparedness and (2) students who experienced learner-centered practices online, supported by contemporary learning theory and community-building course designs and technologies, underwent transformative changes to their learning and identities and feeling confidently qualified for their post study careers. In view of the increasing role e-learning will play in this century, we believe further empirical research of this kind into a myriad of global, digital learning contexts, could help transform online learning and learners in our new post pandemic reality.