Recent dramatic increases in the number of youth arrested for nonserious behavior in schools have led some jurisdictions to search for solutions to the "school-to-prison pipeline." In this article, we evaluate the WISE arrest diversion program in Utica, New York. We use a mixed-methods evaluation design including: (1) a pre–post program comparison of school conduct by participants, (2) a pre–post program comparison of school-based arrests at Upstate High School, (3) a multivariate analysis that estimates the influence of the WISE program on school-based arrests while controlling for citywide juvenile arrests and the passage of time, and (4) interviews conducted with students, program staff, and stakeholders. Although the program appeared more successful in reducing Upstate High School’s reliance on arrest than in improving school conduct among participants, results suggest that the WISE arrest diversion program contains promising elements and lessons for narrowing the school-to-prison pipeline.