Guided by conservation of resources theory, we propose that both organizational and community embeddedness are associated with increased work-to-family conflict (WFC) and family to-work conflict (FWC), which in turn are associated with strain-related outcomes. Because stress can have both short-term and long-term consequences, we examined negative mood as an immediate reaction to stress and chronic insomnia as a longer-term reaction to stress. We examined these relationships in 2-career couples in both the United States (n = 416) and Singapore (n = 400). Results provided full support for the mediating effects of WFC and FWC in the U.S. sample, with only limited support for those mediating effects in the Singaporean sample. In addition, we found that the effects of community embeddedness on FWC were significantly stronger in the U.S. sample than in the Singaporean sample.