Using administrative data from a large 4-year public university, we show that male students are 18.6 percent more likely than female students to receive favorable grade changes. These gender differences cannot be explained by observable characteristics of the students, instructors, and the classes. Surveys of students and instructors reveal that regrade requests are prevalent, and that male students are more likely than female students to ask for regrades on the intensive margin. We corroborate the gender differences in regrade requests in an incentivized controlled experiment where participants receive noisy grade signals, and where they can ask for regrades: we find that males have a higher willingness to pay (WTP) for regrades. Almost half of the gender difference in the WTP is due to gender differences in confidence, uncertainty in beliefs, and the Big Five personality traits.