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The transition from primary school to secondary school is viewed globally as a crucial period in students' lives and a challenging transition can have both short-term and long-term consequences for the wellbeing of students. Despite primary-secondary transition being so important, it is a neglected area of research in general in most countries including South Africa. By smoothing the transition from primary to secondary school challenges that are related to students' disengagement with education, school failure (school dropout), and continued social inequality can be addressed. In this chapter, the value of a transition intervention based on peer mentoring to ease the transition of students in five primary schools in an area of the country where the context is characterized by socioeconomic challenges is discussed. A lack of resources and funding make it difficult to provide individual support to all these students. In response to this challenge, a peer-mentoring approach has been applied to develop an intervention aimed at preparing the students with insight into the challenges that awaits them. The intervention encompasses a workshop attended by a representative group of 20 Grade 7 students, selected based on the leadership skills as demonstrated in their interactions with adults and peers. Following the workshop, they are given the opportunity to give feedback to their Grade 7 peers and also avail themselves for individual discussions with their peers. In this chapter, we critically reflect on the value of this peer-mentored approach for socioeconomically challenged school contexts.