The purpose of the study was to identify the student’s perspective of the difficulties of transitioning from eighth grade to high school. The intent of gathering this information was to provide primary source data for additional study and development of effective transition experiences for students entering the ninth grade. The study identified five primary areas of concern gleaned from previous research and used a survey to quantify student responses to discover which areas were of most concern to students. The research included demographic information to compare male responses to female responses; the responses of students who had an older sibling attend high school to the responses of students who were the first in their family to go through this transition; and the responses of students from a low performing, high poverty, highly ethnically diverse school setting with students from a high performing, low poverty, and less ethnically diverse school setting. The population for the study included 285 eighth grade students from two different middle level schools. The study revealed both new and significant findings as well as insightful information from students in regard to their perceptions of the challenges associated with the transition from eighth grade to high school.