This study set out to provide a descriptive yet critical exploration of teachers’ experiences while using e-learning in the context of the 2019 novel coronavirus (COVID-19) pandemic. Using a qualitative phenomenology research paradigm, the study explored first-hand experiences of three university teachers (hence researchers as well) from two countries, that is, Bangladesh and Saudi Arabia. The contexts in which the researchers used e-learning showcased complex, challenging, and dynamic sites, that is, within institutions and individual classrooms. More specifically, the study identified acceptances, struggles, and negotiations at both the macro-level of policy/decision making and the micro-level of online classroom practices. Reflecting on the findings, this article concludes by offering a set of recommendations that might be applicable and useful for similar contexts beyond Bangladesh and Saudi Arabia. The researchers argue for developing a context-based, inclusive, and appropriate e-learning policy guideline that could be utilized during the emergency time now and in the near future.