Research has identified several aspects that influence students’ transitionto mathematics studies at university, but these aspects haveoften been studied separately. Our study contributes to the field’sunderstanding of the transition between upper secondary and universitymathematics by taking a multifaceted perspective not previouslyexplored. We analyse experiences and attainment in mathematicsof 154 engineering students with respect to known aspectsof this transition, and our results show that it is important to considerseveral aspects together in order to understand the full complexity ofthe transition. It is revealed that students with previous experiencesof university studies, when compared with new first year undergraduates,perceive a larger difference between studying mathematics atthe upper secondary level and university. Our results also show thatthe engineering students enrolled in distance programmes experiencelarger differences between secondary and tertiary levels thanengineering students enrolled in campus programmes. Furthermore,our analyses show that students’ success in mathematics is relatedto their perceptions of the rift experienced in the transition. In all,our results highlight the importance of taking a student perspectivein the development of explanatory and useful models of students’transition between upper secondary and university mathematics.