The expression of personality pathology differs between people and within a person in day-to-day life. Personality pathology may reflect, in part, dysregulation in basic behavioral processes. Thus, a useful approach for studying maladaptive trait expression comes from literature on stress and daily hassles, which provide dynamic accounts for the relations between individual differences and maladaptive dysregulation. This study sought to integrate maladaptive traits and dynamic stress processes to further dynamic models of personality pathology. In a combined clinical/community sample ( N =297) oversampled for interpersonal problems, we used ecological momentary assessment (observation N =19,968) to investigate how maladaptive traits moderated the processes of stress generation, stress reactivity, and affective spillover/inertia. Tests of our preregistered hypotheses provided a mix of supportive and null findings for stress processes identified in past research, and mixed support for the moderating role of personality. The results provide insights into the relations between everyday stressors and personality pathology.