We examine whether anticipated gender discrimination—specifically, gendered sanctions for leadership failure—decreases women’s leadership ambitions. We find that laypeople expect that women leaders will be punished more harshly for failure than otherwise similar men. We also compare the leadership ambitions of women and men under conditions of benign and costly failure and find that leadership roles with costly failure—which implicitly have the potential for gendered sanctions for failure—disproportionally depress women’s leadership ambitions relative to men’s. Anticipated sanctions for failure mediate this effect, providing evidence that anticipated gender discrimination reduces women’s leadership ambitions. These results illuminate microlevel foundations of the stalled revolution by demonstrating how gendered beliefs about leadership are recreated, legitimized, and contribute to the dearth of women leaders. These findings also suggest that organizational responses to failure may produce gender differences in leadership ambitions and risk-taking behavior.