Leaving school without graduating presents a significant challenge for young people and for society as a whole. One way communities and school systems are responding to this challenge is with coordinated efforts to re-engage young people in ways that make it more likely for them to earn a diploma. Re-engagement efforts vary across the country but typically involve identifying young people who have, or are at risk of leaving school before graduating, sharing existing re-enrollment options with them, supporting their re-entry into an appropriate educational setting, and providing supports to propel them toward graduation and, ultimately, success in adult life. To understand the barriers and supports to re-engagement and subsequent academic success in Tucson, Arizona, the Center for Promise spoke directly with Tucson youth who are re-engaging with their education. The Center sought to understand why the youth disengaged from their education, why some youth re-engaged while others did not, what factors contributed to or deterred this re-engagement, and what factors contributed to their persistence through high school graduation. Insights from these youth illustrate the vast challenges they face as well as the supports that can help put young people back onto positive educational pathways.