This study aims to compare students’ perceptions of the digitalization of higher education over time. We hypothesize that the perception will become more positive throughout a study program because of more exposure over time. We applied a 31-item questionnaire in a longitudinal study setting to measure the change in perception. Results indicate data protection, teaching quality, collaboration between students, and training for the digital learning platform as major areas of change in perception. Interestingly, students do not perceive a change in their study success. We conclude that data protection especially needs attention from Higher Education Institutions. Trust, which students experience in the physical space, needs to be transferred to the digital space.