The aim of this study was to explore the way young people facing severe and multiple disadvantage and their support workers perceive the circumstances of the young person. The leaders of 11 U.K. and five U.S. support-providing organisations identified 30 young people aged 16 to 25 who were in great need and 35 workers for this study. Thematic analysis of the semi-structured interviews found that shame was a primary emotional reaction to severe and multiple disadvantage. A history of poor relationships led them to develop an acute assessment of others and a tendency to back away from help. Over time, they perceived themselves to be unworthy and unable. Findings underscored the young people's role in shaping their trajectories and shone light on the role of emotions in explaining disconnection from support.