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Description: Decades of studies identify personality traits as prospectively associated with life outcomes. However, previous investigations of personality characteristic-outcome associations have not taken a principled approach to covariate use or other sampling strategies to ensure the robustness of personality-outcome associations. The result is that it is unclear (1) whether personality characteristics are associated with important outcomes after accounting for a range of background variables, (2) for whom and when personality-outcome associations hold, and 3) which background variables are most important to account for. The present study examines the robustness and boundary conditions of personality-outcome associations using prospective Big Five associations with 14 health, social, education/work, and societal outcomes across eight different person- and study-level moderators using individual participant data from 171,395 individuals across 10 longitudinal panel studies in a mega-analytic framework. Robustness and boundary conditions were systematically tested using two approaches: propensity score matching and specification curve analysis. Three findings emerged: First, personality characteristics remain robustly associated with later life outcomes. Second, the effects generalize, as there are few moderators of personality-outcome associations. Third, robustness was differential across covariate choice in nearly half of the tested models, with the inclusion or exclusion of some of these flipping the direction of association. In sum, personality characteristics are robustly associated with later life outcomes with few moderated associations. However, researchers still need to be careful in their choices of covariates. We discuss how these findings can inform studies of personality-outcome associations, as well as recommendations for covariate inclusion.