Objective In the United States, Hispanic adolescents are at elevated risk for negative outcomes related to risky sexual behavior. To evaluate potential protective factors for this group, we examined the fit of the Hispanic Paradox for sexual behavior among high-risk youth and the moderating role of parent monitoring. Method We enrolled 323 justice-involved Hispanic youth (73% male; mean age 16 years), and measured generational status, parent monitoring (monitoring location, who children spend time with outside of school, family dinner frequency), and sexual risk behavior. Results There were no main effects for generational status on sexual behavior. Parent monitoring of location moderated the relationship between generational status and sexual behavior, such that greater monitoring of location was associated with less risky sexual behavior, but only for youth second generation and above. Conclusions Rather than direct evidence supporting the Hispanic Paradox, we found a more nuanced relationship for generational status in this sample.