Research has demonstrated that experiences with attachment to and psychological separation from parents predict men's reports of masculine gender-role stress and conflict. This article extends the literature by examining possible variations in these links that may be accounted for by men's core personality characteristics. The author hypothesizes that Big Five personality traits mediate the association between parental relationship quality and masculine role strain. Results from structural equation modeling with data from 307 young men generally were consistent with these hypotheses, with several key findings: (a) Replicating past research, the author observed several associations between parental relationship quality and masculine role-strain variables; (b) as expected, indirect effects were obtained for neuroticism, agreeableness, and conscientiousness, though those for openness and extraversion were not statistically significant; (c) comparison of alternate models suggested that a fully mediated model fit the data reasonably well; and (d) this model accounted for a large proportion of variance in masculine role strain (41%). (Contains 2 table and 2 figures.)