This quasi-experimental study examined the effectiveness of a combined tutoring and mentoring intervention for urban, low-income Black youth during the transition to high school. Participants were 118 ninth-grade students (experimental n = 69; comparison n = 49). After 7 months in the intervention program, students in the experimental group showed significant improvement in grade point average, perceived support for educational commitment and attainment, and perceived support from school. Results indicate that this approach was beneficial for these students through the transition to high school and may eventually increase high school graduation rates among these urban youth by helping with this pivotal adjustment to ninth grade.