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Self-regulation (SR) and negative problem orientation (NPO) have well-established, independent connections to psychopathology. Despite theoretical overlap and past empirical work suggestive of a connection between SR and NPO, their relationship has yet to be investigated. This study is the first to examine the potential interactive influence of these constructs on two differing forms of psychopathology: attention-deficit/hyperactivity disorder (ADHD) and depressive symptoms. Undergraduate students aged 18-24 completed the Self-Regulation Questionnaire, Social Problem-Solving Inventory-Revised, Center for Epidemiologic Studies Depression Scale-Revised, and Adult ADHD Self-Report Scale. As expected, SR and NPO were found to be inversely related to each other and independently predictive of ADHD and depressive symptoms. Interestingly, their interaction differentially impacted the two assessed symptom sets. Individuals who had both lower SR and higher NPO reported the highest levels of depressive symptoms, above and beyond the effect of either construct independently. Further, the impact of each construct on depressive symptoms depended on levels of the other construct. In contrast, the interaction between SR and NPO did not significantly affect ADHD symptoms. Lower SR and higher NPO were associated with higher levels of ADHD symptoms regardless of each other. These findings help to characterize the interactive influences of SR and NPO on psychopathology and highlight the need for continued investigation.