Interview, self-report, peer report, and observational data were used to examine parent and peer relationship qualities as predictors of relative changes in attachment security in a community sample of adolescents followed from ages 14 to 24. Early maternal supportive behavior predicted relative increases in attachment security from adolescence to adulthood, whereas psychological control and interparental hostile conflict predicted relative decreases. Peer predictors of relative increases in security included collaborative and autonomous behaviors and lack of hostile interactions, with peer predictions growing stronger for relationships assessed at later ages. Overall, models accounted for sufficient variance as to suggest that attachment security across this period is well explained by a combination of stability plus theoretically predicted change linked to social relationship qualities.