This study researched students' perceptions of their adult relationships at school within the Check and Connect™ mentoring program. This research delved into the impact on fostering students' engagement and promoting academic success within a multi-tiered system of support (MTSS) at a suburban high school in Canterbury County, Florida. The current study investigates students' perceptions of their experiences as they were intentionally paired with adults (mostly teachers but also community members-at-large) at school. In this study, students shared their experiences of interactions with adults at school in the Check & Connect™ Program. Students who participated in the study were compared with matching students who qualified but did not participate. Participating students are those whose school disengagement behaviors led to early warning signs for the at-risk tendencies associated with dropping out of school. Criteria for entry into the program included referrals, screenings, and students' attendance data, behavior referrals, and low achievement. In this mixed methods study, eight students were interviewed about their experiences. Quantitative data were collected from the control and experimental groups by analyzing the changes in attendance percentages, math achievement, English Language Arts achievement, and behavior referrals over an academic year. Qualitative data were collected from semi-structured interviews of students participating in Check & Connect™ for one year who experienced growth in the program. The results of this study provide evidence the Check & Connect™ program had a positive impact on students' attendance, math, ELA, and behavior data. The qualitative results disclosed student perceptions recognizing that their engagement behaviors are related to their academic performance, the importance of having an open, trusting, nonjudgmental relationship with their mentors, and the changes they made to their behavior that influenced their success at school. Recommendations were made based on the results. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com/en-US/products/dissertations/individuals.shtml.]