High dropout rates in the first year of undergraduate studies are an expression of the secondary–tertiary transition problem and they seem to be particularly high in those degree programs where specialized mathematics courses are taught in the first year of study. Research shows that students’ difficulties during the transition period cannot be reduced to purely cognitive factors. In this article, we address the secondary–tertiary transition problem in mathematics for engineering students. Based on a questionnaire with focus beyond the purely cognitive aspects, a comparison of the transition problem at three European mid-sized universities is carried out, to identify common challenges and difficulties, as well as differences. The questionnaire concentrates on the four dimensions (personal, organizational, content related, and social) and corresponding critical requirements for a successful transition described in Trautwein, C., & Bosse, E. (2017). The first year in higher education – critical requirements from the student perspective. Higher Education, 73, 371–387. A group of 308 first-year engineering students partook in the study. In the presentation, we highlight students’ perceptions regarding the transition, changes, and challenges they experienced under the above-mentioned four dimensions and discuss similarities and differences between countries.