This paper proposes that gender differences in responses to recruitment rejections contribute to women’s underrepresentation in top management. We theorize and show that women are less likely than men to consider another job with a prospective employer that has rejected them in the past. Because of women’s status as a negatively stereotyped minority in senior roles, recruitment rejection triggers uncertainty about their general belonging in the executive domain, which in turn leads women to place greater weight than men on fair treatment and negatively affects their perceptions of the fairness of the treatment they receive. This dual process makes women less inclined than men to apply again to a firm that has rejected them. We test our theory with three studies: a field study using longitudinal archival data from an executive search firm, a survey of executives, and an experiment using executive respondents testing the effects of rejection on willingness to apply to a firm for another position. The results have implications for theory and practice regarding gender inequality at the labor market’s upper echelons, highlighting that women’s supply-side decisions to “lean out” of competition for senior roles must be understood in light of their previous experiences with employers’ demand-side practices. Given the sequential nature of executive selection processes, rejection-driven differences in the willingness to compete in a given round would affect the proportion of available women in subsequent selection rounds, contributing to a cumulative gender disadvantage and thus possibly increasing gender inequality over time.