The phrases “engagement in school” and “school connectedness” are cited often in both lay and academic circles, as an essential component of education. This research explores the notion that active and authentic engagement of all students, but in particular those most at-risk, can be achieved through enhancing the pedagogical practice of teachers. The issue of student (dis)engagement is addressed through a case study of small teams of teachers and their students in one secondary school, through a focus on their teaching practice and the students'' perception of that practice that goes beyond narrow ideas of students being on task and complying with teachers'' wishes. I ask (how) pedagogies that engage at-risk students can improve their educational outcomes for students. This research argues that a connected or generative pedagogy, which has at its core students'' backgrounds and lived experiences, will improve student educational outcomes for all but in particular for those nominated as at-risk students. I conclude that such a pedagogy will Connect to students'' backgrounds, Engage with their differences, Respond to real life needs and Empower students agentically in their lives.