Across the globe, the emergence of COVID-19 led to widespread, sudden suspension of in-person instruction, displacing more than 1.5 billion learners (Capilla et al., 2020). Addressing the gap in research on emergency remote teaching (ERT), this empirical study draws on insights from semi-structured interviews with 10 in-service and five pre-service teachers, who navigated the transition both as K-12 teachers and graduate students, participating in weekly mentoring for English language learners, online curricular modules, face-to-face discussions (until the transition to ERT), mixed-reality simulation teaching with coaching, and written reflections. Using a sensemaking theoretical framework, our study examines the following questions: (1) What were the main challenges and opportunities of ERT as experienced by this cohort of language teachers? (2) How did the dual role of being a K-12 teacher and graduate student provide a unique lens for navigating these challenges and opportunities? (3) What tools or supports helped these language teachers through the transition to ERT? Thematic analysis revealed three themes (emotion, shared meaning, and technology) and illuminated connection as an overarching theme. Findings suggest that the experience of navigating the transition from both positions led to greater empathy, increased facility using technology, and a growing support network of fellow teacher-learners.