Rural youth are now graduating from high school at rates comparable to their peers in urban and suburban schools, however far fewer rural youth pursue postsecondary education. Using a comparative case study method, we explore postsecondary preparation efforts at three rural school districts. Each case represents a different classification of rural: fringe, distant, and remote. We find that while all three districts offered similar postsecondary preparation programs, the amount and array of available course offerings and levels of additional support provided by the community differed. We also explore how the values and philosophies of school administrators shaped the postsecondary preparation efforts. These findings are considered through the lens of previous research on factors that influence the educational outcomes of rural youth, including literature on rural brain drain.