Traditionally, a large lecture hall course follows a teacher-centered approach to instruction. This was the case for the "gateway" course in the undergraduate Information Technology and Informatics (ITI) major in the School of Communication and Information at Rutgers, The State University of New Jersey. This paper describes the journey and collaboration between the course instructor and the instructional design/technology specialist to transform a large lecture hall course (with up to 450 students) into an active, collaborative learning experience--one that engages students in learning, emphasizes higher-order thinking skills, and creates a sense of community that can be lacking in such a format. This transformation was realized when the boundaries of the classroom extended into the "online" environment.