A combination of age and gender factors shape older women’s workplace experiences. Age advocacy groups, together with many academic commentators, argue in favor of workplace flexibility, pointing to benefits for both older workers and their employers. But knowledge about the policies of organizations and how they are enacted by managers is still rudimentary. What do managers understand flexibility to mean and how do they implement flexible working options? What are the perceived benefits and costs of flexibility for organizations and for older women workers? Drawing on qualitative interviews conducted with 58 human resource managers, this article considers the provision of flexible working arrangements targeting older women in Australia within 3 industry sectors: financial services, public sector, and higher education. Interviews revealed a gap between policy and practice regarding the management of older women workers. We argue that the efficacy of line managers and their willingness to innovate are crucial in managing such workers and prolonging their working lives.