This article explores the role of selected work-based constructs and social support in the prediction of school engagement in a sample of Italian high school students. A total of 137 high school students from Central Italy completed measures of social support (including teacher, peer, and parental support), career decision-making satisfaction, career planfulness, and school engagement, each of which had been translated to Italian from English. The results reveal that high levels of career decision-making satisfaction, career planfulness, and teacher support were statistically significant predictors of school engagement. The findings are discussed in relation to career development theory, educational and counseling practice, and prevention.