While study success and completion rates are important issues in educational policy, research highlights the particular relevance of the first year in higher education (HE) for students' future academic performance and achievement. In Germany, the recent reform of degree programmes appears to have created new challenges related to students' transition to HE, yet little is known about the specific requirements students perceive as critical for their first-year experience. The present study, therefore, seeks to explore the first-year challenges in German HE from the student perspective focusing on the nexus of the individual and institutional factors relevant for successful transition. Following the critical incident technique, data collection consisted of semi-structured interviews with 25 students from all six faculties of a German university. We employed the qualitative content analysis to examine first-year challenges in terms of the critical requirements emerging from the interviews. First, the thematic analysis of the data resulted in identifying a broad range of personal, organisational, content-related and social requirements students perceived as critical for transition to HE. Second, the quantitative analysis of code occurrence suggested that personal and organisational requirements are most relevant from the students' perspectives. Finally, the single-case analysis of the interviews disclosed that individual students experience an accumulation of first-year challenges revealing the interconnectedness of critical requirements. In sum, the findings offer a systematic overview of the first-year challenges as well as provide detailed insights on how the interplay of institutional and individual factors contributes to the transition to HE.