Conducted from a social-pedagogical perspective, this study, which is based on biographical analyses, focuses on the question of how education and learning in a broad sense are connected to the academic education of children and youth in out-of-home care. Two case examples of young women who left residential care in Germany (selected from a sample of fifteen cases) highlight different patterns of biographical learning and different connections between biographical and academic learning. The results emphasize that situations of biographical crisis can clearly be an obstacle to successful school attendance. At the same time, if a biographical learning process has taken place, it is very likely that education will be successfully resumed.