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Research has begun to demonstrate the benefits of mindfulness and self-compassion for military veterans. However, investigation has lacked on how a prominent feature of military culture, adherence to masculine norms, may impact veterans’ experiences of these practices. This research examined the interrelationships among masculinity, mindfulness, and self-compassion as well as how these variables predict well-being (coping and quality of life) in 164 military veterans. Veterans completed all study measures via an online survey. Results demonstrated that mindfulness and self-compassion both predict better coping and quality of life and are related to lower adherence to masculine norms. Masculinity was found related to less active coping, more avoidant/negative emotionality coping, and worse mental health-related quality of life. The Masculinity subscale of Success Dedication, however, was associated with greater mindfulness and active coping and better quality of life. Exploratory results demonstrated a significant moderation effect in which mindfulness predicted greater active coping for veterans with low masculinity but not for veterans with high masculinity. This study provides preliminary data on the role of masculine norms in the context of mindfulness and self-compassion. Although findings link total masculinity scores to negative outcomes, the masculinity component of Success Dedication appears to be a point of commonality between masculinity and mindfulness. Therefore, an effective strategy for clinicians may be to begin the teaching of mindfulness by emphasizing elements that appeal to veterans’ norms of success.