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This article describes a nearly decade-long partnership between three institutions representing school, public, and academic settings in Westchester County, New York. The program, designed to improve the academic performance of local high school students, is unique due to the extensive contact students have with academic librarians during the school year, including two day-long orientations and individual consultation sessions. Using experiences as partners in this collaborative effort, interviews with six teachers and librarians, and the existing literature, this article identifies best practices and key factors for academic libraries that are considering or currently providing instructional and outreach activities to high schools.