Why do women receive equal or better performance ratings than men in managerial assessment centers even when they are structured in ways that systematically disadvantage them? This study provides the first attempt to understand this managerial assessment center gender paradox using in-depth interviews with managerial assessment center evaluators for a large semi-military governmental organization. The study revealed that the managerial assessment center was a gendered environment in which organizational practices, language used, and the underlying logic establish and reinforce men as assertive or protectors and women as weak and in need of protection. In accordance with the managerial assessment center gender paradox, women were successful at the managerial assessment center despite systemic bias against them. Interpretive analysis revealed that women candidates generate discomfort that evaluators alleviate by increased attention to the extent to which they conform to gender ideology. We coin the term ‘benevolence effect’ to describe evaluators’ tendency to over-valuate and advance women candidates who conform to traditional stereotypes of white femininity. The benevolence effect paradoxically contributes to the preservation and perpetuation of the sexual binary and the idealization of the abstract manager as male-bodied in the organization, even as it contributes to the promotion of women.