Depression is frequently considered a disorder of impaired affect regulation with deficits across both positive and negative affective systems. However, where deficits in emotion regulation occur in youth, specifically regarding regulation of positive emotions, is relatively unknown. The current study tested whether deficits in broad (felt and expressed) and specific (up-regulation and maintenance) positive emotion processes are associated with youth depressive symptoms. Adolescents (n = 134; 65 girls) in grades 7 to 9 completed a self-report measure of depressive symptoms prior to participating in two parent–child interactions tasks, a rewarding trivia task and a problem-solving conflict task. During the interaction tasks, adolescent’s overall self-reported experience and observed expression of positive affect (PA) was examined. Following the reward task, youth’s ability to up-regulate PA (PA response) and maintain PA while buffering against NA (PA persistence) was explored observationally. Results suggested that reduced experience and expression of PA was associated with depression symptoms, but only in a context that elicited negative emotions. No association was found between PA response and depression symptoms; however, shorter PA persistence was associated with elevated depressive symptoms. Youth higher in depressive symptoms appear able to respond similarly to rewarding events, but fail to maintain PA and ward off NA when transitioning from a positive to negative task.