Although past studies of mentoring at-risk youth have yielded mixed results (Faith et al., 2011; DeWit et al., 2016), mentoring as an intervention for at-risk youth has increased in the past decade and has been supported by the United States Federal Government (Hughes, Boyd, & Dykstra, 2010; Gordon, Downey, & Bangert, 2013; Reddick, Griffin, & Cherwitz, 2011). Because studies focused on the perceptions and experiences of mentors are limited (Hughes et al., 2010; Haddock et al., 2017), and because of frequency of early mentor/mentee relationship termination (Grossman et al., 2012; Golder, 2016), this qualitative study sought to capture and understand the voices of the mentors. Using in-depth interviews, program training materials, and written reflections by the mentors, this study explored the perceptions, experiences, and meaning-making of 11 college students who had volunteered to mentor at-risk K-12 youth for a minimum of two years. The study's setting was a 33-year-old site-based mentoring program in Russellville, Arkansas, known as Age to Age. Findings in the study relate to (a) motivations to begin and continue mentoring; (b) role conceptualization; (c) benefits and challenges of mentoring; (d) overcoming the challenges of mentoring; (e) meaning assigned to mentoring; and (f) how mentors experienced program components and processes. Findings may inform mentor recruitment, training, retention and may also inform educational leaders who work with at-risk youth. The theoretical underpinning for this study was Self-Determination Theory (Ryan & Deci, 2017). The study also implicates the importance of understanding rejection sensitivity (McDonald et al., 2010; Grossman et al., 2012). [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://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]