Background: The transition from school to higher education (HE) involves multiple challenges including academic issues, motivation and identity adaptation. In this scenario, the role of family, peers and institutions can be fundamental in the success of the transition process. Purpose: We sought to deepen our understanding of the transition phenomenon by studying students' perceptions on HE expectations versus the reality encountered, identifying the main challenges they faced and analysing the strategies used to cope with the difficulties encountered in adjusting to HE. Method: This is a follow-up interview study that examined the perceptions of 14 first- and second-year HE students in Chile, who had participated in a previous research study two years earlier whilst in secondary school. Interview data were analysed using a qualitative approach. Findings: The analysis identified contrasts between students' expectations and what occurred during the first two years of HE. Associated with academic difficulties, the students felt that the main challenges included increased complexity of content, time management and study strategies. To cope with these challenges, the evidence suggested that the students adapted their academic strategies and relied strongly on their families and peers. Conclusions: Our findings draw attention to a mismatch that can occur between the expectations and the reality that students face once they have transitioned to HE. Implications for institutions include building a transition bridge between secondary and postsecondary education, which goes beyond providing information about funding or the labour market. In terms of supporting successful transition, issues such as academic demand, studying time, study strategies and prior familiarity with HE staff and peers are all relevant aspects for consideration.