Recent emergent research is seriously questioning whether parental strictness contributes to children’s psychosocial adjustment in all cultural contexts. We examined cross-generational differences in parental practices characterized by warmth and practices characterized by strictness, as well as the relationship between parenting styles (authoritative, indulgent, authoritarian, and neglectful) and psychosocial adjustment in adulthood. Parenting practices characterized by warmth (affection, reasoning, indifference, and detachment) and strictness (revoking privileges, verbal scolding, and physical punishment) were examined. Psychosocial adjustment was captured with multidimensional self-concept and well-being (life satisfaction and happiness). Participants were 871 individuals who were members of three generations of Spanish families: College students (G3), their parents (G2), and their grandparents (G1). Results showed two different cross-generational patterns in parenting practices, with an increased tendency toward parental warmth (parents use more affection and reasoning but less indifference across generations) and a decreased tendency toward parental strictness (parents use revoking privileges, verbal scolding, and physical punishment less across generations). Interestingly, despite cross-generational differences in parenting practices, a common pattern between parenting styles and psychosocial adjustment was found: indulgent parenting was related to equal or even better self-concept and well-being than authoritative parenting, whereas parenting characterized by non-warmth (authoritarian and neglectful) was related to poor scores.