Digitalization of teaching, learning, and assessment in higher education has gained increasing attention in research in the recent years. While previous research investigated issues of effectiveness, course attendance, and course evaluation from a long-term perspective, the current COVID-19 pandemic forced higher education institutions to digitalize teaching, learning, and assessment in a very short time. In this context, we investigate the effects of the digitalization of three courses from operations research and management science in the summer term 2020, namely two large lectures and tutorials for undergraduate, and a seminar for graduate students. To that end, student performance, course and exam attendance rates, and course evaluations are compared to the setting of the same courses in the previous year 2019 with a traditional, non-digitalized setting. Next to the quantitative data, qualitative statements from the course evaluations and students’ expectations expressed during the term are investigated. Findings indicate that the lecturers’ understanding of learning behavior has to develop further as interaction is required in any format, on-site or digital. Absenteeism and procrastination are important risk areas especially in digital management education. Instruments would have to be adapted to digital settings, but with care and relating to course specifics (including digital evaluation). Digital education does not make learning per se easier or harder, but we observed that the students’ understanding and performance gap increased in digital teaching times. As an outlook, we propose the longitudinal investigation of the ongoing digitalization during the COVID-19 pandemic, and going beyond, investigate opportunities of the current crisis situation for implementing the long-term transition to digital education in higher institution institutions.