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Background: Alcohol and substance use among young people is a well-documented public health concern, and is particularly prevalent in college populations. Problematic internet use is also an emerging issue, with potential negative effects on academic achievement. University dropout remains a critical challenge, especially among freshmen, with research highlighting the role of academic engagement factors such as motivation, self-efficacy, and university connectedness in students’ academic trajectories. Methods: This study explored the relationships among risky substance use, problematic internet use, academic engagement factors, and academic outcomes, identifying potential mediators. Freshmen from an Italian university were invited to complete an online survey assessing these variables. The study defined two academic outcomes: (i) academic performance (Grade Point Average, GPA) and (ii) dropout intentions. Spearman’s rho coefficients and multiple linear regression models examined the associations among risky substance/internet use, academic engagement factors, and academic outcomes. Mediation analyses assessed whether academic engagement variables mediated the relationship between risky substance/internet use and academic outcomes. Results: The results showed that only problematic internet use was significantly associated with GPA, with self-efficacy and lack of motivation fully mediating this relationship. Regarding dropout intentions, problematic internet use and the risky use of alcohol, cannabis, and sedatives were directly and positively associated with dropout intentions. Several motivation subscales, self-efficacy, and university connectedness mediated these relationships. Conclusions: These findings highlight the role of academic engagement factors in mitigating the impact of risky behaviors on students’ academic trajectories, emphasizing the need for targeted prevention and intervention strategies.
