Background To ensure successful medical education despite the COVID-19 pandemic, the demand for online instruction has substantially increased. Fast and efficient teaching in a digital format poses a great challenge for medical students and lecturers as well as the universities. Objective The aim of this study is to capture the readiness of medical students and faculty members to participate in rapidly- evolving online education. Methods This cross-sectional study is based on two questionnaires distributed among medical students and associate deans for education in Germany, Austria and Switzerland. Questions included decision- making questions, categorical questions, and open-ended questions, all addressing the frequency and format of the digital education offered, the perceived quality of digital education, and medical student satisfaction with digital education. Questions about missing content and areas for improvement from the perspectives of medical students were included. The associate deans were asked for their opinions about the impact of the pandemic on teaching, the organizational setup and implementation of digital education by universities, and plans for future initiatives. Results Three thousand and thirty medical students (m = 752 and f = 2245) from 53 universities participated in the study. The study showed that 92% of students were affected by the pandemic, and 19% of the students viewed the changes as entirely negative. 97% of the medical students were able to participate in digital courses, but only 4% were able to learn exclusively online. For 77% of the medical students, digital offerings accounted for over 80% of the education offered. In terms of content, medical students complained about a lack of practical teaching, such as contact with patients, lecturers, fellow medical students, and a poor perceived quality of teaching due to dubbing, frequent changeover of seminars, problem-oriented learning groups and in-person teaching, a lack of interaction possibilities and a lack of technical equipment, such as lecturers’ knowledge and server capacities, at the universities. Overall, almost half of the medical students (42%) rated the implementation of digital teaching at their universities as good or very good. Forty-one of the 53 associate deans responded to the questionnaire, and 35 felt medical education was influenced by the pandemic. The associate deans (80%; 33/41) felt that the digitalization of medical education was negatively influenced by the pandemic. Only 44% (18/41) felt that their universities were well or very well positioned for digital teaching. All the associate deans believe that digital teaching in medicine will continue after the pandemic. Conclusions In the German-speaking world, the rapid conversion of medical teaching to a digital format has been well implemented in many cases. The perceived quality of the implementation of digital education still lacks practical relevance and the use of new digital media, such as learning games, VR, and online question time. The digital format of medical education will likely continue beyond the COVID-19 pandemic.