Drawing on developmental contextual theory, the authors examined the relationship of perceived barriers and support with school engagement and vocational attitudes among 9th-grade urban high school students in 2 studies. Study 1 (N= 174) showed that both perceived barriers and perceived support from family kin were associated with youths' commitment to school and aspirations for success in their future careers. Study 2 (N= 181) replicated and extended Study 1, demonstrating that perceived barriers, general perceptions of support, and kinship support were associated with behavioral and attitudinal indexes of school engagement, as well as with aspirations for career success, expectations for attaining career goals, and the importance of work in one's future. The findings contribute to efforts to identify individual and contextual factors relevant to the educational and vocational lives of urban minority youth.