Research has shown that a developmental process of maturing out of alcohol involvement occurs during young adulthood, and that this process is related to both young adult role transitions (e.g., marriage) and personality developmental (e.g., decreased disinhibition and neuroticism). The current study extended past research by testing whether protective marriage and personality effects on maturing out were stronger among more severe late adolescent drinkers, and whether protective marriage effects were stronger among those who experienced more personality development. Parental alcoholism and gender were tested as moderators of marriage, personality, and late adolescent drinking effects on maturing out; and as distal predictors mediated by these effects. Participants were a subsample (N = 844; 51% children of alcoholics; 53% male, 71% non-Hispanic Caucasian, 27% Hispanic; Chassin, Barrera, Bech, & Kossak-Fuller, 1992) from a larger longitudinal study of familial alcoholism. Hypotheses were tested with latent growth models characterizing alcohol consumption and drinking consequence trajectories from late adolescence to adulthood (age 17-40). Past findings were replicated by showing protective effects of becoming married, sensation-seeking reductions, and neuroticism reductions on the drinking trajectories. Moderation tests showed that protective marriage effects on the drinking trajectories were stronger among those with higher pre-marriage drinking in late adolescence (i.e., higher growth intercepts). This might reflect role socialization mechanisms such that more severe drinking produces more conflict with the demands of new roles (i.e., role incompatibility), thus requiring greater drinking reductions to resolve this conflict. In contrast, little evidence was found for moderation of personality effects by late adolescent drinking or for moderation of marriage effects by personality. Parental alcoholism findings suggested complex moderated mediation pathways. Parental alcoholism predicted less drinking reduction through decreasing the likelihood of marriage (mediation) and muting marriage's effect on the drinking trajectories (moderation), but parental alcoholism also predicted more drinking reduction through increasing initial drinking in late adolescence (mediation). The current study provides new insights into naturally occurring processes of recovery during young adulthood and suggests that developmentally-tailored interventions for young adults could harness these natural recovery processes (e.g., by integrating role incompatibility themes and addressing factors that block role effects among those with familial alcoholism).