Parental knowledge attenuates delinquency in adolescence and may be particularly effective in low-resourced environments. Moreover, parenting behaviors in one generation may influence subsequent generations’ psychosocial adjustment. In this pilot study with data spanning three generations, we explored whether the first generation’s (G1; n = 48) parental knowledge throughout the second generation’s (G2; n = 48) adolescence was associated with the third generation’s (G3; n = 60) psychosocial adjustment outcomes. Further, we examined potential mediators and moderators of the links between G1 parental knowledge and G3 outcomes. G1 parental knowledge predicted lower G3 depressive symptoms, anxiety, risky behaviors, and poor self-control. Although mechanisms remain unclear given non-significant mediation models, socioeconomic hardship moderated the association between G1 parental knowledge and G3 anxiety.