Using 2 waves of the Wisconsin Longitudinal Study, I examine psychological consequences of potentially stressful, non-normative, or "off-time" aspects of the parental role in late midlife and early old age, including coresidence with adult children, stepparenthood, and parental bereavement. Additionally, I analyze gender differences in psychological implications of these characteristics of parenthood. Findings from random-effects pooled time-series models indicate that having stepchildren is unrelated to older parents' mental health. Moreover, the psychological consequences of step-parenthood do not depend on parental gender or the quality of parent-child relationships. Conversely, having at least 1 coresidential adult child of post-college age decreases psychological well-being among mothers but not among fathers. Death of a child has a detrimental effect on parents' mental health; yet, fathers are affected more adversely than mothers. The findings are interpreted with respect to family stress, parental role, and gendered role perspectives. Distinct experiences of this cohort of mothers and fathers are discussed.