Mobility has become more constrained, and patterns of immobility are spatially concentrated in certain parts of the United States. Drawing on three years of ethnographic fieldwork in Mississippi, this article examines the role of college as a pathway out of this entrenched poverty and the social and structural barriers that limit the potential of higher education for poor students. It argues that for rural youth, especially rural youth of color, enrolling in college and finding employment that uses that education requires a permanent transition from one opportunity structure to another, a transition that is not often expected of students from more privileged backgrounds. This transition creates social, psychological, and cultural barriers that limit students' ability to be mobile through education.