Early quantitative analyses of Emergency Remote Teaching framed faculty experience through the dichotomy of “curse” versus “opportunity,” yet such labels obscure the lived processes underlying these judgments. This qualitative pilot study adopts a narrative inquiry approach to examine how specific “critical incidents” shaped faculty interpretations of digital teaching during the COVID-19 emergency. Analyzing in-depth narrative responses from a purposive sample of four university professors across Southern Europe, the study identifies two divergent narrative archetypes. The “opportunity” narrative is triggered by moments of unexpected inclusion, in which digital tools enabled participation from previously marginalized or introverted students, producing pedagogical epiphanies. In contrast, the “curse” narrative is driven by experiences of isolation and loss of non-verbal feedback, conceptualized as a “void of feedback” consistent with Transactional Distance theory. These findings suggest that faculty acceptance of digital teaching is not primarily determined by technical competence, but by emotionally charged relational experiences. The study argues that sustainable digital professional development must prioritize strategies that foster connection and social presence, increasing the likelihood of positive turning points while mitigating experiences of disconnection.