This study investigated the relation between emotional autonomy, as measured by Steinberg and Silverberg's Emotional Autonomy Scale (EA), and adolescent adjustment as moderated by several individual, familial, and cultural contexts. Subjects were 96 adolescents (10–18 years old) and their mothers and teachers. Results indicate that when the affective nature of the parent-adolescent relationship is positive (e.g., maternal warmth is high or intensity of parent-adolescent conflict is low), positive adolescent adjustment is more likely when adolescents report less emotional autonomy. On the other hand, when the family environment is more stressful, emotional autonomy is positively associated with adolescent adjustment. Findings suggest that higher scores on the EA scale index emotional detachment from parents and that such detachment is detrimental in supportive familial environments but adaptive in less supportive familial environments. That emotional detachment from parents appears to serve a protective function in certain stressful situations is viewed as analogous to the adoption of an avoidant attachment strategy during infancy.