Rural students graduate from high school at higher rates but go to college at lower rate than their urban and suburban peers. To take on the educational attainment challenge for rural students, we need to know more about postsecondary encouragement programs. This study examined a pilot postsecondary encouragement program in 11 rural high schools with two questions: How do high school counselors support students' plans for life after high school through a land-grant outreach program? How is a university outreach program utilized in these schools? This qualitative case study used 17 individual interviews with school counselors and county extension agents. According to school counselors, the postsecondary encouragement program increased financial aid applications and student interest in college going. County extension agents were a trusted bridge between the program and the local high schools. Tracking student milestones helped school counselors serve all students, and program experts provided workshops for students and parents. Campus visits helped students visualize themselves as college students, yet financial concerns dominated the students' college choices.