Stress associated with acculturation and minority status among Hispanic youth is understudied. Using survey data from the Hispanic Stress Inventory-Adolescent Version (HSI-A), we examined psychosocial stress across eight domains including family economic stress and acculturation-gap stress in a national sample of three generations (first, second, and third or higher) of Hispanic adolescents ("N" = 1,263). Research questions addressed generation differences in frequency of stressor events (i.e., discrimination), appraisal of these events, and mental health symptoms. Results indicated that experiences of different categories of stress were significantly related to generation status. The first generation reported more stressors and greater stress appraisal than the third-generation adolescents. Similar levels of discrimination stress were reported by participants regardless of generation. The second-generation participants reported a greater number of Acculturation Gap Stressors than the third generation, and more delinquent and aggressor behaviors than first-generation participants. An acculturation paradox was found with greater stress exposure and stress appraisals in the first-generation youth, but with lower mental health symptoms than later generations. Family integrity and more traditional family values may buffer the negative impact of greater stressor exposure among immigrants and second-generation youth when compared with third-generation adolescents.