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Amidst rising concerns that high school seniors are not as prepared for college, the number of programs to support the first year students has increased. The present study examined the perspectives of two groups of students, two high school seniors applying to college and ten college freshmen in their second semester. Both groups of students participated in peer-mentoring programs that included sessions addressing college adjustment, major and career paths study skills, and time management. Surveys consisting of college preparedness, peer mentoring and topic helpfulness and interest scales, and open response questions regarding their experiences were completed. Additionally, the high school students were given in-depth open response questions regarding the weekly mentoring topics. The undergraduates reported on remedial courses completed. Analyses suggested the peer-mentoring programs increased students' understanding of behaviors that lead to college success. They also suggested that high schools might need to focus on honing the skills needed to succeed in college. Understanding what skills the soon-to-be first year students and matriculated college students need to be academically successful is imperative so that staff and instructors may appropriately assist and guide students toward the goal of earning college degrees.