This study aimed to investigate whether work-family enrichment (WFE) would strengthen the positive effects of family supportive supervisor behaviors on organizational citizenship behaviors (OCBs), and to examine whether the frequency and the intensity of the moderating effects would differ according to the targets and contents of each variable. Participants were 350 married employees from dual-income families who had an immediate supervisor. Results indicated that WFE had significant moderating effects on the relationships of emotional support and instrumental support, two subtypes of family supportive supervisor behaviors, with OCBs. Regarding the subtypes of OCBs, moderating effects were more observed in the model on OCB directed towards other individuals which stemmed from interpersonal sources, sharing the matching content and domain as family supportive supervisor behaviors. Furthermore, among the three subtypes of WFE (i.e., development, affect, and capital), capital WFE showed the highest frequency of moderating effects, and the intensity of significant moderating effects also varied depending on the predictor subtypes to interact. Based on these findings, we discussed academic and practical implications and suggestions for future research.