This study explores the occupational aspirations of high school students planning to attend college by drawing on a multilayered model of college enrollment, social cognitive career theory, and multiple descriptive case studies of 15 high schools. Students' occupational aspirations and their understanding of the education required to achieve these aspirations appear to be connected to the resource level of schools in this study. The nature of career programming provided also varied by school resource level, illustrating how multiple layers of context shape the development of students' career interests as well as their decision making with respect to educational and career choices. (Contains 2 tables and 1 figure.)