In this paper we explore the difficulties engineering undergraduates encounter with tertiary mathematics. Results from our survey (N = 71) show that students in our sample face issues mostly related to the challenging nature of university mathematics, the absence of worked examples during lectures and the discontinuity of school and university mathematics curricula. By using third generation Activity Theory, we were able to interpret the identified difficulties as contradictions emerging between the school and university activity systems as well as within the university activity system, and we argue that these difficulties can be treated as stemming from the structural characteristics the two activity systems have.