Parents’ use of conditional regard as a socializing practice was hypothesized to predict their children’s introjected internalization (indexed by a sense of internal compulsion), resentment toward parents, and ill-being. In Study 1, involving three generations, mothers’ reports of their parents’ having used conditional regard to promote academic achievement predicted (a) the mothers’ poor well-being and controlling parenting attitudes, and (b) their college-aged daughters’ viewing them as having used conditional regard, thus showing both negative affective consequences from and intergenerational transmission of conditional regard. Study 2 expanded on the first by using four domains, including both genders, and examining mediating processes. College students’ perceptions of their mothers’ and fathers’ having used conditional regard in four domains (emotion control, prosocial, academic, sport) were found to relate to introjected internalization, behavioral enactment, fluctuations in self-esteem, perceived parental disapproval, and resentment of parents. Introjection mediated the link from conditional regard to behavioral enactment. The results suggest that use of conditional regard as a socializing practice can promote enactment of the desired behaviors but does so with significant affective costs.