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School-based mentoring (SBM) programs are seen as a way of preventing the disengagement of young people from education. However, existing research points to a complex relationship between SBM programs and improved engagement outcomes. There is therefore a need for greater understanding of the pathways through which SBM leads to outcomes for young people. This paper addresses this complexity, examining the nuanced ways in which SBM may lead to positive outcomes for young people. Drawing on the qualitative perspectives of 15 young people engaged in an Australian SBM program, the findings point to two types of pathways to outcomes. First, direct pathways go to the heart of young people's engagement, by prioritizing educational performance and achievement as the focus of the mentoring relationship. Second, holistic pathways see mentors seeking to influence young people's broader thinking about the value of education, their wellbeing and their communication skills, to in turn address issues that may otherwise present barriers to young people's engagement. The paper discusses the policy implications of the findings. It highlights the importance of acknowledging and measuring incremental steps to improved educational engagement, in a context of young people experiencing non-linear and complex pathways to engagement outcomes. [ABSTRACT FROM AUTHOR]