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This article examines how gendered workplace characteristics are related to workers’ access to flexible workplace policies and expectations of access to flexible workplace policies. Two studies are used to examine why women prefer occupations that are “family friendly” but concentrate in occupations that have low access to flexible workplace policies. First, multilevel survey data are used to examine how gendered occupational characteristics are related to access to flexible workplace policies. Findings indicate that women experience a significant flexibility penalty in women-dominated occupations because of high sociability requirements and low occupational authority. Although women were found to experience a flexibility penalty due to job characteristics typically found in female-dominated occupations, a survey experiment shows that women expect that workers will have greater access to flexible workplace policies in occupations with feminine-typed traits compared to occupations with masculine-typed traits. Taken together, the results support my claim that false notions of feminine-typed work as family friendly can contribute to women’s concentration in occupations with low wages and few organizational resources.