This research proposes a self-handicapping process in which people proactively endorse negative in-group stereotypes when there is the prospect of failure in a task. In Experiment 1, we found that women were more likely to endorse the math-gender stereotype stigmatizing their gender group when they anticipated a difficult versus easy math task. In Experiment 2, the same pattern was observed among men stigmatized with relatively poor verbal skills. In Experiment 3, we found that such a self-handicapping tendency was most prominent among individuals with high trait self-esteem, who are presumably more motivated to maintain self-esteem versus those with low trait self-esteem. All together, these results suggest that endorsing negative in-group stereotypes can be used as an anticipatory coping mechanism, occurring even before receiving failure feedback in the presence of a high risk of failure.