This chapter presents testimonials of 12 national experts in the field of educational technology concerning the main didactic, technological, and social challenges they faced throughout the “emergency remote teaching” that occurred during the COVID-19 pandemic confinement. All experts are professors in Portuguese universities or polytechnic institutions, and they are acquainted with the “distance education” modality. An online questionnaire was applied to these 12 professors in order to collect their opinions about the main challenges during this period. Based on a content analysis technique, the results revealed several technological (e.g., unpredictability of internet connections), didactic (e.g., the teachers' lack of technological pedagogical content knowledge), and social challenges (e.g., the lack of proper physical spaces at home). Based on the lessons learned from this worldwide pandemic emergency, and critically reflecting about it, recommendations are suggested for future action to “distance education” in higher education.