The Transition-to-Success Mentoring Act amends the Elementary and Secondary Education Act of 1965 to create a new grant program. This program empowers the Secretary of Education to award funds to eligible entities for establishing, expanding, or supporting school-based mentoring initiatives. The primary goal is to assist at-risk middle school students in successfully transitioning from middle school to high school. Priority for these grants will be given to entities serving high-poverty or high-crime areas, providing postsecondary and career development opportunities, and ensuring long-term mentor-mentee matches. Grant recipients are required to assign each eligible student a "success coach" who will develop a personalized plan for success , involving the student, parents, and school staff. These plans outline academic, personal, college, and career exploration goals, with coaches meeting regularly with students to provide support, identify areas for improvement, and connect them with necessary resources. Funds can also be used for comprehensive training for success coaches, covering topics like trauma-informed practices and cultural competency, as well as for recruiting, screening, and compensating coaches. Additionally, the bill authorizes funds for inclusive youth engagement activities, such as career awareness events and visits to higher education institutions, and for program evaluation. Eligible entities must submit annual reports detailing student participation, demographics, academic achievement, dropout rates, and social-emotional development. The Secretary of Education is mandated to provide interim and final reports to Congress on the program's success. Furthermore, the Secretary will collaborate with the Office of Juvenile Justice and Delinquency Prevention to offer grantees access to mentoring resources and information on transitional services for specific student populations.