School attendance problems and school dropout are recognised as a major concern by researchers, policymakers, practitioners and the wider society. Although research acknowledges the multi-faceted complexity of dropping out of school, only a limited number of studies have focused on the perspective of support workers (e.g., teachers, social workers, school management, student coaches, policymakers, researchers, labour consultants and psychologists). Using in-depth interviews with 32 support workers, this study reveals an integrated insight into the process of dropping out and its affecting factors. The results of this study provide a conceptualisation of dropping out, and 6 themes emerged from the data, shedding light on the intrapersonal, interpersonal and contextual influencing factors. The study suggests the recognition of the complex interplay of risk factors, the development of a positive discourse to overcome stigma, and the contextualisation of practice based on the holistic educational needs of students to 'do whatever it takes'.