Drawing on data from the 2008 U.S. National Study of the Changing Workforce, this study (1) examines the associations between access to three types of flexible working arrangements-flextime, flexplace, and culture of flexibility-and psychological distress, (2) tests the mediating roles of work-family conflict and work-family enrichment, and (3) investigates whether these relationships differ by workers' childcare or elder-care obligations as they intersect with gender. Results show that a flexible workplace culture, but not access to flextime or flexplace, is associated with lower psychological distress. Work-family conflict and work-family enrichment partially mediate the relationship between culture of flexibility and psychological distress. In addition, the negative effect of culture of flexibility on psychological distress is stronger among workers sandwiched between preschool childcare and elder-care compared with those with neither caregiving obligations, a pattern especially pronounced among women. We discuss these results and their implications for organizational practices and worker well-being.