Research has demonstrated the stability of juvenile offending during childhood and adolescence but generally has not focused on the continuity of family interactions associated with juvenile offending. The present report focused on the stability of several family interaction events and attributes (i.e., physical punishment, communication, supervision, positive parenting, and parent–child relationship) for a large sample of male adolescents and their primary caretakers, drawn from a multiyear longitudinal study that represented middle childhood through late adolescence (ages 6–18). We also assessed the impact of ethnicity, family composition, teenage motherhood, and youth delinquency on these interactions. Test–retest correlations and growth-curve analyses were used to assess relative and absolute stability of the interactions, respectively. As predicted, relative stability of family interaction was high. There was an absolute change in scores of physical punishment (decreased) compared to poor supervision and low positive parenting (both increased), whereas poor communication and bad relationship with the caretaker did not measurably change with age. Single-parent families and families with teenage mothers experienced significantly worse interactions over time than did families consisting of two biological parents present in the household. These findings are discussed in relation to the development of juvenile offending.