Our study examines how the relationships with various human ecological systems influence the transition by rural students from home communities to postsecondary institutions. Using phenomenological interview data with 14 students who are from rural Alaska and 14 postsecondary student service staff, our analysis identified characteristics of the postsecondary transition processes that seem particular to rural students--in navigating urban places and cultural norms, seeking institutional supports, advocating for self, and forming new social relationships. In all of these experiences, rural identities and community-oriented values emerged as a guiding force for students' goal-setting, decision-making, interactions, and adjustment. Our data suggest opportunities to reinforce connections and cooperation among human ecological systems to improve the postsecondary transition experience for rural students.