Individual differences in positive affect (PA) are related to a host of salient developmental outcomes, including social functioning, physical health, and psychopathology. One factor that may contribute to individual differences in PA involves individual differences in PA regulation, which may be broadly categorized into strategies to enhance PA and strategies to dampen PA. To date, however, factors contributing to individual differences in youth PA regulation have been largely understudied. Thus, the present study examined associations between youth depressive symptoms and (a) the implementation and (b) the effectiveness of enhancing and dampening regulation in daily life settings. Participants included 146 early adolescents (52.1% girls; ages 10–14; M[SD] = 12.71[.86]). Youth depressive symptoms were measured using self-report on the CDI-SF. Youth PA and use of enhancing and dampening regulation were assessed 3–4 times per day for a period of 9 days using smartphone-based experience sampling methods (31 total assessments). Results of multilevel structural equation models indicated that depressive symptoms predicted individual differences in youth implementation of dampening but not enhancing regulation. Cross-level interaction analyses indicated that depression did not predict the effectiveness of enhancing or dampening regulation in modulating youth subsequent PA. Findings indicate that youth reporting more depressive symptoms engage in greater dampening of PA relative to their peers, but that PA up- and down-regulation strategies are no more or less effective among early adolescents experiencing elevated levels of depression. Results have implications for understanding mechanisms of risk and resilience across development.