This article examines the patterns of resistance to norms of masculinity (i.e., emotional stoicism, physical toughness, and autonomy) and its association to psychological and social adjustment among boys from preadolescence through late adolescence. Semi-structured interviews were conducted longitudinally with a sample of 55 White, Black, Latino, and Chinese American boys from 6th grade to 11th grade. Our analyses indicated that boys' resistance to norms of masculinity is explicit and implicit and is prevalent during adolescence, with 78% of the boys in our study demonstrating moderate to high levels of resistance typically during the middle school years. Four trajectories of resistance over time were detected: (a) decreasing resistance; (b) stable moderate-to-high levels of resistance; (c) stable low levels of resistance; and (d) mixed patterns of resistance. White, Black, and Chinese American boys were the most likely to suggest a decline in resistance from pre-to late adolescence, whereas the Latino boys were the least likely to suggest such a decline and the most likely to suggest stable moderate-to-high levels of resistance throughout adolescence. Findings suggest that resistance to norms of masculinity enhances psychological and social adjustment for boys during adolescence and is deeply influenced by the context in which boys are embedded.