University and secondary school educators recognize many high school students will undertake a post-secondary education but find themselves unprepared for the academic demands once they arrive on campus. Although many high school students appear to possess basic abilities in retrieving information, particularly when searching the Internet, they often lack the critical evaluation skills needed to succeed at the college level (Jackson & Hansen, 2006). Developing the necessary information literacy skills among high school students to support a successful transition to college is a unique undertaking for any institution. The authors provide a case study of an outreach effort between an academic library and an urban high school during challenging budgetary times. Lessons learned from the development of their information literacy instructional program and the instructional tools created will be discussed. Student outcomes within the collaboration which include the development of research and critical thinking skills necessary to succeed after high school will be addressed as well. This collaboration may serve as a model for other institutions developing similar programming. (Contains 2 figures.)