This paper illuminates and details some of the traits, pressures and semi-autonomy of the young adult between the ages of 18 and 24 who must confront the barriers and challenges upon returning to secondary school within the high school and the adult education centre context. Focusing on these young adults is fundamentally important to begin to understand and appreciate the many variables such as gender, early school-leaving, re-entry and needs that impact students who are re-entering secondary school. We present the negative experiences that many of our young adult students have had in a manner that is summative yet touches on the underlying socio-economic challenges that have forced their hand and placed them not only at risk but caused them to leave the secondary school program before program completion. A number of personal insights and qualitative collective observations present an accurate picture of the situation in one central Ontario (Canada) site.