Gang involvement is an increasing issue among Latino youth, yet nuanced research on its potential causes is scarce. Quantitative and qualitative data were used to explore links between acculturative stress and gang involvement among immigrant and U.S.-born Latino middle school students (N = 199). Regression analyses showed that U.S.-born youths were more likely to be gang-involved if they experienced discrimination stress, but less likely to be gang-involved if experiencing adaptation stress. Neither form of stress predicted gang involvement among immigrant youth; however, several reported economic inequality as a difference between themselves and Americans. Those reporting inequality were more likely to be gang-involved than those who did not. These findings suggest gang involvement may work differently for U.S.-born and immigrant Latinos.