Teachers implementing tutoring programs in which their students with emotional and behavioral disorders (EBD) serve as cross-age tutors (CAT-EBD) for younger students in need of additional instruction have reported improvements in academic, social-emotional, and behavioral skills for both tutees and tutors. This practitioner-lead article features firsthand experiences and insights from a special educator implementing such a program. In addition to identifying the perceived strengths, challenges, and overall outcomes of a CAT-EBD program, the experiences within the case study highlight connections and recommendations for effective planning, training, supervising, and supporting of students with EBD as tutors. Practical strategies are provided in support of the challenges identified in implementing and sustaining a CAT-EBD program.