Adolescence is an important stage for the development of emotion regulation skills, especially for adolescent girls who are at elevated risk for the development of depression and anxiety. Although some emotion regulation strategies are more effective at helping adolescents regulate negative affect on average, research indicates strategy effectiveness varies with the context in which a strategy is deployed. Yet less work has been done examining which contextual factors are associated with adolescents switching emotion regulation strategies in their daily lives. This study examined individual and contextual factors related to negative interpersonal events that are associated with strategy effectiveness, including age, emotional intensity, perceived controllability, and co-regulatory support, and their association with adolescent emotion regulation strategy switching in daily life via ecological momentary assessment. Results indicated that adolescent girls differed in the degree to which they altered their emotion regulation strategies throughout their daily lives, and that switching strategies was associated with age as well as individual and within-person differences in perceived controllability, emotional intensity, and co-regulatory support. This study provides critical proof-of-concept of the utility of emotion regulation strategy switching as a measure of regulatory flexibility and highlights regulatory processes that may hold clues to the mechanisms of developmental psychopathology.