Distance learning technology continues to grow and undergo significant changes in higher education settings. Applying strategic planning methods from organizational behavior and operations management can act as a useful guide for the implementation of a sustainable distance learning program. Strong planning can help ensure the distance learning program system's operational readiness, effectiveness, and sustainability. Distance learning operations planning requires a defined strategy that examines organizational human and technical structures. We discuss a distance education planning approach applied to three higher education cases with a goal of improving their distance education efforts. The research contexts were in the United States of America: a small Midwestern university seeking to grow online programs in support of its competitive strategy, a large western university with established distance programs, and a regional community college. This article will illustrate the use of business-oriented, systems thinking models for evaluation and distance education program improvement.