--- - |2 Mothers of 317 first‐time juvenile offenders (M = 15.35 years old) were interviewed over 2.5 years about their expectations and aspirations for their sons' futures. Mothers' expectations were lower than their aspirations, reflecting a discrepancy between what mothers felt was important for their child's future and what they considered likely to happen. As their children continued to engage in delinquent acts, mothers' expectations for their sons' future success diminished. Youth age moderated the association between delinquency and maternal expectations, such that when perceived delinquency was high, expectations were lower for mothers of young sons compared to mothers of older sons. These findings carry implications for practice and intervention, as parent expectations and aspirations are both directly and indirectly associated with youth achievement. - Journal of Research on Adolescence, EarlyView.