This study examined the efforts of a large, urban school district to reduce future occupational disengagement risks by requiring all high school students to complete 60 hours of work-based internships. The hypothesis was that social support from adult supervisors and mentors positively affected students' occupational engagement orientations over and above the influence that programmatic experiences provided. The survey data for this study were collected from all seniors in the district's 17 high schools (N = 1,741). Ordinary Least Squares (OLS) was applied in a hierarchical regression in four stages. The findings indicated that opportunities to receive social support, especially having a mentor, contributed most to seniors' future dispositions toward occupational engagement. District career and technical education (CTE) students also experienced greater social support than non-CTE students. The recommendations focused on the need for comprehensive high schools to provide more access to supportive adults and personalized supportive learning environments. (Contains 2 figures and 4 tables.)