This article describes Aspire, a new motivational interviewing (MI) early intervention program designed to prevent dropout among students repeating the ninth grade, and then examines the feasibility and acceptability of this program through a mixed-methods approach. The Aspire program is a nine-lesson curriculum grounded in MI with an emphasis on skill development. Thirteen students repeating the ninth grade from three high schools participated in the Aspire program. Students completed a survey at the beginning and end of the program. School social work trainees also completed implementation checklists and participated in a focus group. Students reported being satisfied and finding the intervention helpful in promoting school-related skills. Nine of the thirteen students remained in school. Most Aspire lessons were implemented with high fidelity. Feasibility issues related to the flexibility of the curriculum and the amount of contact time with students. These findings document the promise of MI as a feasible and acceptable strategy for working with students who are repeating the ninth grade in an effort to prevent high school dropout. These findings also demonstrate the importance of feasibility and acceptability studies for future refinement of the Aspire program and the design of rigorous effectiveness studies.