Young people from families of low SES are substantially less likely to complete high school than those from families of high SES. Most of the research has centred on why these young people become disengaged. In contrast, this study examines what triggers and processes lead disengaged young people from nine low-SES NSW high schools to turn-around and re-engage with learning. Of the 2,000 Year 7-9 students involved in this longitudinal mixed-methods study, 119 young self-identified through the survey and interview data obtained in the first year, that they had low levels of motivation, were disengaged at school, and wanted to leave school before completing Year 12. We followed these young people through annual interviews across three years. By selecting cases in which students participated in both surveys and interviews over all three years, a sample of 55 was obtained who had longitudinal survey and narrative data. This data showed that 23 (41.8%) of them had turned around and became more engaged. That is, these young people showed consistent gains between Time 1 and Time 3 engagement measures adopted from the Motivation and Engagement Scale (MES) (Martin, 2003) that resulted in a one standard deviation increase to at least four of the five MES measures. Follow-up interviews at Time 3 substantiated their classification as more engaged given they articulated and confirmed a shift in their self-perceptions and attitude towards learning. There were however, 13 (23.6%) young people who had no overall change and 19 (34.5%) young people who reported lower levels of engagement showing declines by one standard deviation in the MES measures. With notable numbers remaining disengaged it is important to understand and learn from what rendered the 23 initially disengaged young people to turn-around and re-engage in learning. The findings reveal that turning-around involves a two stage process. The first entails a conversation or event that serves as a trigger for change. Various triggers were identified and these experiences were instrumental to leading the young person to think differently about themselves and altered their perceptions of learning. These changed perceptions were insufficient unless they were accompanied by steady, long-term processes that served the purpose of sustaining their new directions. This two-staged process of turning-around will be discussed as will the implications for teachers and schools.