Adult–child relationship factors were examined to determine whether they differentiated between individuals who follow expected versus unexpected educational pathways. Low-income participants (96 men, 83 women) in the United States were followed from birth through age 23. Individuals were identified who followed expected versus unexpected pathways to high school graduation or dropping out based on academic achievement and behavioral problems. Patterns of parental involvement in school were significantly different between expected dropouts and unexpected graduates in middle childhood. In contrast, expected graduates had higher levels of parent involvement in middle childhood, more supportive parent–child relationships in early adolescence, and higher levels of social competence with adults than unexpected dropouts.