Prior investigations have demonstrated that parents' religiousness is related inversely to adolescent maladjustment. However, research remains unclear about whether the link between parents' religiousness and adolescent adjustment outcomes--either directly or indirectly via adolescents' own religiousness--varies depending on relationship context (e.g., parent-adolescent attachment). This study examined the moderating roles of parent-adolescent attachment on the apparent effects of the intergenerational transmission of religiousness on adolescent internalizing and externalizing symptoms using data from 322 adolescents (mean age = 12.63 years, 45 % girls, and 84 % White) and their parents. Structural equation models indicated significant indirect effects suggesting that parents' organizational religiousness was positively to boys' organizational religiousness--the latter of which appeared to mediate the negative association of parents' organizational religiousness with boys' internalizing symptoms. Significant interaction effects suggested also that, for both boys and girls, parents' personal religiousness was associated positively with adolescent internalizing symptoms for parent-adolescent dyads with low attachment, whereas parents' personal religiousness was not associated with adolescent internalizing symptoms for parent-adolescent dyads with high attachment. The findings help to identify the family dynamics by which the interaction of parents' religiousness and adolescents' religiousness might differentially influence adolescent adjustment.