Tertiary transition in mathematics appears to be an insurmountable strugglefor many students, including for high achievers in secondary school. The high dropoutrates in many Western Countries represent a big issue from an individual and socialpoint of view. It appears particularly significant to analyse this phenomenon in thecontext of the degree course in Mathematics, studying students’ cognitive and affectivereactions to the (often unexpected and severe) difficulties encountered in the tertiarytransition. With this aim, we developed a narrative study in a specific context in Italy—that involves excellent students from secondary school—to investigate how successfuland dropout students describe their experi ence in transition. Implications for theeducational practice are discussed.