As high schools begin to offer more distance learning courses, universities have an opportunity to establish partnerships to deliver online IT courses. Delivering online courses at the high school level, however, means overcoming obstacles that may not be faced at the university level. In particular, establishing partnerships with high schools requires politically savvy navigations of bureaucratic roadblocks while ensuring the integrity of course content and delivery. This chapter provides a primer on establishing relationships with high schools to deliver college-level IT curriculum to high school students in an asynchronous learning environment. We describe the curriculum introduced and discuss some of the challenges faced and the lessons learned.