This research examines whether and when leader optimism—a trait perceived as both feminine and leadership-positive—yields different evaluations for female versus male leaders. Drawing on goal-based stereotyping theory, we propose that observers interpret identical optimistic behavior differently based on leader gender, and that observers' power positions critically shape these interpretations. Across three studies, including analyses of startup pitch competitions (Study 1, N = 463) and two experiments (Study 2, N = 427; Study 3, N = 541), we find that female leaders face penalties for displaying optimism while male leaders do not. This penalty is particularly pronounced when observers hold higher-power positions, as these observers tend to attribute women's optimism to gender-typicality rather than leadership capability. The effects are explained through observers' perceptions of leaders' competent agency and emotional control. Interestingly, female leaders receive more favorable evaluations when displaying lower optimism, particularly from higher-power observers who view them as more emotionally controlled. These findings reveal how the same leadership trait can yield different outcomes based on leader gender and observer power, contributing to our understanding of subtle barriers women face in leadership roles.