This study examined the hypothesis that maternal socialization of coping would make a differential contribution to youth depression and externalizing psychopathology depending on youths' level of exposure to life stress. A sample of 155 youth (M age = 12.41, SD = 1.21) and their maternal caregivers completed semi-structured interviews and questionnaires in a two-wave longitudinal study over a 1-year period. Results provided evidence for two types of socialization x stress interactions--an amplification-effects model and a differential-effects model. In the context of interpersonal stress, findings supported an amplification-effects model wherein the risk and protective effects of engagement and disengagement socialization of coping emerged in youth exposed to high but not mild levels of stress. In the context of noninterpersonal stress, findings supported a differential-effects model wherein disengagement socialization of coping contributed to heightened risk among youth exposed to high stress but dampened risk among youth exposed to mild stress. This research identifies maternal socialization of coping as a noteworthy contributor to risk for youth psychopathology, and highlights the need to consider parenting x environment interactions when investigating parenting processes related to youth psychopathology.