A large body of research demonstrates that women encounter severe penalties for violating gender stereotypes. In this paper, we explore the conditions under which the reverse is true—when being subject to a stereotype can actually benefit a woman compared to a man who is not subject to the same stereotype. In particular, we suggest that in situations of causal ambiguity—uncertainty about the reasons that a behavior occurred—differences in how men and women are evaluated will be moderated by the extent to which observers engage in a low or a high level of deliberative causal reasoning. In 3 experimental studies, participants were asked to make judgments about an employee who violated a female gender stereotype by failing to provide help to a coworker when asked to do so, but the reasons for this behavior were unclear. When participants were prompted to engage in deliberative causal reasoning, women were evaluated more positively than men, but not in the absence of such a prompt. Moreover, when participants did engage in deliberative causal reasoning, the more positive evaluations of women compared to men were driven by participants' beliefs that women's behavior was due more to situational constraints than the same behavior by men.