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The Pro Se Speech and Debate Program is a student-led engaged learning program at Cornell University, housed within the New York State School of Industrial and Labor Relations (ILR). In this initiative, Cornell undergraduate and graduate students engage with justice-impacted youth (ages 14-17) in Central New York to provide mentorship and educational offerings. Cornell students serve as “speech and debate coaches” and peer mentors to youth involved in the Central New York Health Home Network’s (CNYHHN) “Restorative Integrated Youth Services” (RIYS) diversion program in Utica, New York. The primary goal of the program is to empower youth by building self-advocacy skills tied to supplemental academic opportunities provided by peer-aged mentors. Youth who complete the program receive a certificate of completion in “Speech and Debate” from Cornell and are provided opportunities for campus visits. The program is student-led in several ways, including curriculum design, service delivery, research/evaluation, and continuous improvement efforts. The program just completed its second year. In the first year, twelve youth mentees and seven Cornell mentors participated in a three- to six-month long mentorship—some mentorships were extended beyond the initial three months based on youth benefit and mutual interest in continuing the mentorship. Evaluative data from the first year of the program suggested that over 80% of youth program participants either made progress in their individual goals, or successfully graduated from the program. In the program’s second year, an additional ten youth and six mentors participated in the program with comparable progress and completion rates. Despite the program’s successes, the experiences of mentors varied significantly, with some mentors experiencing challenges engaging youth. Evaluation data for the project comes from a mentee survey administered at the beginning and end of the program, a mentor “checklist” administered monthly, and administrative data from the community partner. In addition to evaluation data, this paper provides three Cornell students' experiences as mentors, to offer an additional source of qualitative programmatic information in the form of case studies of mentor successes and challenges. By design, the paper presents case studies from mentors who experienced: (1) significant youth engagement; (2) mixed youth engagement; and (3) low youth engagement. The goal of providing these perspectives is to gain experiential insight into barriers, facilitators, and strategies for increasing engagement. As such, the case studies span much different experiences working with youth, which are typical of the program.