In recent work, we showed that putatively adaptive emotion regulation strategies, such as reappraisal and acceptance, have a weaker association with psychopathology than putatively maladaptive strategies, such as rumination, suppression, and avoidance (e.g., Aldao & Nolen-Hoeksema, 2010; Aldao, Nolen-Hoeksema, & Schweizer, 2010). In this investigation, we examined the interaction between adaptive and maladaptive emotion regulation strategies in the prediction of psychopathology symptoms (depression, anxiety, and alcohol problems) concurrently and prospectively. We assessed trait emotion regulation and psychopathology symptoms in a sample of community residents at Time 1 (N = 1,317) and then reassessed psychopathology at Time 2 (N = 1,132). Cross-sectionally, we found that the relationship between adaptive strategies and psychopathology symptoms was moderated by levels of maladaptive strategies: adaptive strategies had a negative association with psychopathology symptoms only at high levels of maladaptive strategies. In contrast, adaptive strategies showed no prospective relationship to psychopathology symptoms either alone or in interaction with maladaptive strategies. We discuss the implications of this investigation for future work on the contextual factors surrounding the deployment of emotion regulation strategies.