This article provides an insight into ethnic inequalities in education, from the point of view of successful students with an immigrant background. Since the 1990s, educational and migration studies have examined the unexpected pathways of disadvantaged students: researchers tested different hypotheses concerning drivers of success, highlighting social, family, and institutional mechanisms that have reproduced inequalities but also generated new opportunities. The educational success of students with a migrant background, however, is under-investigated in Italy, which represents a relevant context in which to explore the coexistence of persisting educational drawbacks and successful schooling for the children of migrants, born in Italy or abroad. Using data from a qualitative study carried out in northern Italy, the analysis is based on autobiographies written by an heterogenous group of 65 students of immigrant origin attending different types of upper secondary schools. The analysis reveals the presence of different meanings, attitudes, and narratives of success among these students, which vary according to the different cohorts of immigrant-origin students. Each group implements different successful strategies—standing out, working hard, waiting—inspired by individualistic and collective logics, which can imply specific risks for students and different types of impact on equal opportunities and social cohesion. These findings could open new avenues of research and intervention, helping policymakers and practitioners to think and act, given that success is indeed possible for immigrant-origin students.