Online teaching and learning has evolved over the past two decades into a viable and respected means to higher education, with many undergraduate and graduate courses now offered in this format. While the popularity of online coursework has resulted in increased online enrollment and offerings, often the course design, strategy selection, student workload and learning relevance has lagged behind in comparison. As additional research becomes available into how to motivate and engage the online learner and how to best prepare online courses for optimum student success, universities may be faced with opportunities to redesign already existing online courses to best meet the research-based advances of online teaching and learning. During the 2018-2019 and 2019-2020 academic years, one School of Education at a southeastern university engaged in this very discussion and process of redesigning and transforming already existent online courses. Using the ADDIE (Analyze, Design, Develop, Implement, Evaluate) educational process as a guiding protocol, university leaders, instructors and course designers engaged in aligning online courses in a Master of Arts in Educational Leadership program with best 21st century practices and online learning research. This article outlines a representation of that journey: the research, the reasoning, and the results.