<p>Acculturative stress is experienced by many Latinx adolescents and has been linked to negative behaviors such as rule breaking and substance use. Parental monitoring is thought to serve as a protective factor for adolescent outcomes. Because research shows that the effectiveness of parental monitoring depends on the gender of the child, the current cross-sectional study aimed to analyze the associations between acculturative stress and risky behaviors in the form of rule breaking and binge drinking as well as the potential moderating effects of parental monitoring and gender among 193 Latinx adolescents (M_age = 15.90, SD = 1.47) from rural areas in the Southeastern United States (54% female; 76% U.S.-born). We expected that higher levels of acculturative stress would be associated with higher levels of risky behaviors, and that parental monitoring would weaken this association. We also expected to find gender differences. Utilizing cross sectional data collected via interview surveys, hypotheses were tested using a hierarchical regression model. Results indicated there was a significant positive association between acculturative stress and risky behaviors. This relationship was also significantly moderated by gender and parental monitoring for binge drinking outcomes. Furthermore, there was a significant three-way interaction between acculturative stress, parental monitoring, and gender in predicting binge drinking. These findings illustrate the negative effects of acculturative stress and how parental monitoring can serve as a potential protective factor against problem behaviors such as rule breaking and binge drinking, particularly among Latinx adolescent boys.</p>