As the number of working parents rises, employers are increasingly called upon to support employees’ work–family (WF) obligations. Grounded in conservation of resources theory, we examined how providing varying degrees of parental support (paid vs. unpaid leave and family-supportive vs. -unsupportive leadership) is mutually beneficial to employee and organizational well-being – the ultimate criterion for organizational science. Participants (N = 538) were randomly assigned to read vignettes that varied the amount of parental support provided for expectant working parents. We tested whether WF benefits fairness perceptions moderated the indirect effects of parental support on felt obligation through job-related anxiety. Findings supported our proposed moderated-mediation model, with the most positive effects when full parental support was provided to individuals with high fairness perceptions. Our research highlights the value of providing both paid leave and family-supportive leadership, while also considering employees’ fairness perceptions, to reap the most gains of employee and organizational well-being.