This study examines high school expectancies in a sample of at-risk, rural youth, and how these expectancies relate to 8th grade functioning, 9th grade functioning, and 9th grade experiences of high school. A total of 76 eighth-graders and their parents, drawn from a larger study of the transition to high school, participated in interviews the summer before 9th grade regarding students' expectations about high school. 59 of these students and their parents were again interviewed the summer following 9th grade to examine adjustment to high school. Overall, 8th grade students, such with greater academic competence and a more positive view of the school environment had more positive high school expectancies. High school expectancies did not predict change in socio-emotional functioning in high school, but they were associated with more positive experiences of high school. The study suggests that high school expectations may play an important role in high school experiences, and thus serve as a valid target for programs aimed at easing the high school transition.