Parental monitoring remains a central protective factor against a range of adolescent risk behaviors, including substance use, mental health issues, and negative peer influence. It involves parental awareness and oversight of adolescents’ friendships, activities, and digital behavior Recent scholarship has further advanced this understanding by exploring moderating influences such as neighborhood context, peer relationships, and cognitive factors. Building on this foundation, the present study examines the impact of parental monitoring on adolescent well-being, with a specific focus on the moderating role of school connectedness. This study used the 2021 Youth Risk Behavior Survey (YRBS) to examine the effect of parental monitoring on adolescent well-being mediating for school connectedness. To achieve this, researchers conducted binary logistic regression analyses explored four outcomes: poor mental health, suicidal ideation, hopelessness, and drug use. Across all models, higher parental monitoring was associated with significantly lower odds of negative outcomes. These findings underscore the dual importance of engaged parenting and supportive school environments in promoting adolescent resilience, while also pointing to the need for tailored supports for vulnerable subgroups. Implications, future research, police, and practice are discussed.