This article addresses two fundamental questions about flexible scheduling: Do managers use ascriptive information in deciding which requests for flexible work scheduling to grant among employees? And, do employees comprehend this managerial bias in deciding whether to ask for flexible work arrangements? Study 1 found that managers were most likely to grant flextime to high-status men seeking flexible schedules in order to advance their careers. In contrast, flexible scheduling requests from women were unlikely to be granted irrespective of their job status or reason. In Study 2, we found that employees were unaware of these managerial biases: women assigned high-status jobs and requests for career advancement reasons were the most likely to think their requests would be granted, while men in the same scenarios were least likely to believe this. Organizational and policy implications are discussed.