Background/Context Although much research has dealt with the factors that influence educational expectations, few studies have addressed recent high school graduates who attend community colleges as their first postsecondary institutions. As the costs associated with attending a four-year institution keep rising, community colleges increasingly serve as an affordable entry for many socioeconomically underprivileged students who aspire to earn a bachelor's degree and above. The question of sustaining these educational expectations—an essential precursor to the actualization of educational goals—becomes even more important knowledge to pursue. Purpose/Objective/Research Question/Focus of Study This research investigates socio-demographic, motivational, and postsecondary contextual factors underlying community college students’ baccalaureate expectations. The study highlights various influences affecting these educational expectations of community college students, thus improving the understanding of the relationship among student backgrounds, motivational beliefs, college experience, and the development of baccalaureate expectations. Population/Participants/Subjects This study is based on a nationally representative sample of spring 2004 high school seniors who were part of the second follow-up study of the Education Longitudinal Study of 2002 (ELS: 2002) and who enrolled in a community college as their first postsecondary institution within two years of graduation from high school. Among the 12,500 students of the 2004 senior cohort who completed the second follow-up interview, roughly 3,000 students who attended community colleges as their first postsec-ondary institutions were selected as the study's sample. Research Design The proposed conceptual model was tested by using structural equation modeling (SEM) analysis. After fitting the SEM model for the entire sample and assessing its overall fit, a multiple group analysis was used to ascertain whether the structural model is invariant across gender groups. Findings/Results Results indicate that community college students’ baccalaureate expectations two years after high school were directly and positively influenced by their initial baccalaureate expectations during the high school senior year and their academic integration during the first year of college, but were negatively associated with the number of subjects for remedial work they received. In addition, socio-demographic backgrounds, parental expectations, and motivational beliefs of students indirectly affected subsequent baccalaureate expectations by directly influencing initial expectations. Motivational beliefs also exerted a direct effect on college academic integration, which in turn contributed to students’ subsequent baccalaureate expectations. Conclusions/Recommendations This study illuminates the importance of cultivating positive motivational beliefs, promoting academic integration, and improving remedial practices to help community college students move further toward their educational goals. This knowledge should help community college leaders seek innovative ways to better streamline student choices in alignment with their educational expectations.