In 2009, the University of Chicago Library began offering Library privileges to seniors attending our University-run charter high school, UC Woodlawn (UCW). As part of this new program, the Library provided instruction sessions for the students, who had little experience using academic libraries. The Library experienced several challenges implementing effective programs. Through their experiences, U of C librarians were able to learn from mistakes and develop successful programs working with UCW teachers. At the end of the presentation, participants will be offered an opportunity to share their experiences working with high schools at their libraries.