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Indulgent parenting has been associated with adolescents’ psychological well-being problems; however, prior research has primarily relied on adolescents’ report of such parenting behavior and its association with their own well-being, often overlooking parents’ perceptions of indulgence and their own well-being. In this study, we address this gap in the literature by examining the agreement and disagreement between parents’ and adolescents’ perceptions of indulgent parenting and the implications for the psychological well-being of both adolescents and their parents. Further, we explore the role of adolescent–parent relationship satisfaction as a potential factor affecting these associations. Our investigation was based on data from 128 parent–adolescent dyads. Utilizing structural equation modeling with double-entry intraclass correlations (ICC_DE), our analyses revealed several main findings: (1) adolescents perceived higher levels of indulgent parenting than their parents did; (2) disagreement in perceived indulgent parenting between parents and adolescents was linked to psychological well-being problems for both adolescents and their parents; and (3) disagreement in perceptions in indulgent parenting had a stronger association with adolescents’ well-being problems when adolescents reported greater relationship satisfaction with their parents. These findings provide insights into perceptions of indulgent parenting within parent–adolescent relationships and bring psychological implications for both adolescents and their parents.