Dropping out from school is considered to be a cumulative process of disengagement and it remains a serious concern for educational communities. Current research on school dropout focuses mainly on risk factors and developing evidence-based prevention and intervention programs, although the effectiveness of these programs is not unequivocal. This study aims to disentangle knowledge from experts by experience (i.e., practice-based evidence) about key elements in building engagement (i.e., cognitive, behavioral, and emotional engagement). Thirty-two in-depth interviews were conducted with support workers in an urban area in Belgium. The results of this study uncover seven elements with practice-oriented advice, which expands the triangle of engagement with operationalized strategies to prevent students from dropping out. Overall, this study highlights belonging and connectedness (i.e., emotional engagement) as primary factors. In addition, this research complements the focus of research and practice on the significance of cross-professional collaboration in supporting students.