Individuals who suffer from depression can be stigmatized by labeling and resort to negative stigma coping orientations such as secrecy and withdrawal, resulting in internalized self-stigma. Self-stigma can have negative effects such as low self-esteem, low self-efficacy, isolation, and feeling like a failure. Guided by modified labeling theory, the purpose of this study was to fill a gap in the literature on predictors of two orientations (challenging and deflecting) of positive stigma coping. Challenging stigma involves taking action, and deflecting is a cognitive strategy; both are used to positively cope with the stigma of mental illness. Predictors included symptom severity, depression literacy, stereotype awareness, treatment seeking, social support, and stigma sentiments in a sample of undergraduates (N = 195). Results from a canonical correlation found that individuals with high scores on deflecting and, simultaneously, low scores on challenging tended to have high scores on stigma sentiments and low scores on both symptom severity and treatment seeking. Analyzed in independent regressions, challenging was significantly predicted only by symptom severity (+), while deflecting was predicted by symptom severity (-), depression literacy (+), and stigma sentiments (+). These findings reinforce the potential for individuals who suffer from depression to address stigma using healthier and more affirming coping orientations. Implications for positive social change include a decrease in self-stigma regarding depression, less negative stigma coping, an increased awareness of how depression stigma affects individuals who suffer from the disorder, and a decrease in the social stigma of depression. Educators and practitioners can apply this information in academia, counseling, and clinical practice.