We investigated age-based changes in mothers' complaints about offspring behavioral opposition, and offspring reports of opposition in a prospective longitudinal design (N = 821). Maternal complaints declined from pre-adolescence to early adulthood, but more slowly in low socioeconomic status (SES) and single-parent families. Mothers complained more about first- than later-born children, but showed no average differences for offspring gender, race, SES, or single parent status. Complaints covaried with youth-reported opposition, but effects involving SES, single-parent status, and birth order remained significant after opposition was controlled; this finding is interpreted to reflect social contextual differences in maternal beliefs. Youth opposition was stable to age 16, then decreased; higher levels were associated with earlier birth order and low SES among European-Americans. Our results have implications for parenting interventions, indicating that parents may benefit from education about the normative, gradual increase in concordance between their own expectations and their child's behavior from early to late adolescence. Further, parenting interventions may be strengthened by actively attending to social contextual factors that shape parental belief systems and values.