The current longitudinal study examined the effect of the transmission of maladaptive parenting strategies from grandmothers to adolescent mothers on childrenÕs subsequent development. Mexican-origin adolescent mothers (N = 204) participated in home interviews when the adolescentÕs child (89 boys, 60 girls) was 2, 3, 4, and 5 years old. GrandmothersÕ psychological control toward the adolescent mother was positively related to adolescentsÕ potential for abuse 1 year later, which was subsequently positively related to adolescentsÕ punitive discipline toward their young child. In addition, adolescent mothersÕ punitive discipline subsequently predicted greater externalizing problems and less committed compliance among their children. Adolescent mothersÕ potential for abuse and punitive discipline mediated the effects of grandmothersÕ psychological control on childrenÕs externalizing problems. Finally, adolescent mothersÕ potential for abuse mediated the effect of grandmothersÕ psychological control on adolescent mothersÕ punitive discipline. Results highlight the salience of long-term intergenerational effects of maladaptive parenting on childrenÕs behavior.