Research has robustly demonstrated that children exposed to early ecological adversity are at risk for developing antisocial, externalizing behavior problems (rule breaking, aggression, disregard for others). Yet, studies have also demonstrated multifinality in developmental pathways unfolding in adversity’s aftermath, with many children showing remarkable resilience. Understanding sources of such resilience is critical, especially across different populations (Luthar et al., 2006, 2015). In Family Study (FS, 102 low-risk mothers, fathers, and infants) and Play Study (PS, 186 high-risk mother-toddler dyads), we test a model of parent–child attachment security, observed at 15 months in FS and 2.5 years in PS, as a moderator of effects of early family ecological adversity, assessed as a cumulative score of sociodemographic risks (graded for severity) at 7 months in FS and 2.5 years in PS, on children’s antisocial, externalizing problems, observed and parent-reported at 5.5 years in FS and 7 years in PS. We supported moderation for mother–child relationships in both studies: Higher early family adversity was associated with more antisocial outcomes five years later, but only for children with less secure attachments. We highlight the key role of early security as a protective factor and a source of resilience for children in families experiencing adversity.