Traditionally, accounting has been described as a gendered profession. Recently, accounting firms, and especially the Big Four, have made very public commitments to promote greater gender equality. Yet they struggle to retain women, especially at more senior levels. Drawing on a recent empirical field study of managers in one of the Big Four accounting firms (pseudonym Sky Accounting), we explore the effects of a flexible work initiative that was developed with the aim of creating “the best professional workplace for women”. The paper addresses the flexibility program as a key organizational practice that was specifically designed to enhance the progression and retention of talented women at senior levels. We show how the initiative that was designed to challenge the status quo was, in practice, translated into a mechanism that actually reinforced gender barriers. In order to theorize our findings, we draw on contemporary theoretical approaches to gender from both accounting and organization theory and suggest several critical reflections on the dynamics of bringing about change in relation to gender inequality.