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The fluid boundaries between work and family life and the dynamic ways these domains are shaped by communication technology represents an important area in work-family research. However, surprisingly little is known about how family contact at work affects functioning in the work role. Drawing on longitudinal data from the Canadian Work, Stress, and Health Study (2011-2017), the present study examines the association between family contact and family-to-work conflict. We find that family contact increases family-to-work conflict, but gender and three salient family-related conditions—economic hardship, providing care for family members, and difficulties or strains with children—are key moderators of this focal relationship. We discover that the focal association is significantly stronger for women, those with more economic hardship, caregiving responsibilities, and difficulties with children. We discuss these results by integrating border theory with stress amplification and the cost of caring.