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Degree programs in Information Systems typically include a course on Systems Analysis and Design which is challenging to teach for instructors and challenging to grasp for learners. The central issue is that conditional knowledge, or when to use concepts and techniques in this domain, is seldom, if ever, taught. This chapter explains the ongoing evolution of a course on Systems Analysis and Design with the goal of developing conditional knowledge in students. It follows the process of changing course objectives, developing expert models of problem solving, experiencing challenges in delivering this kind of content, and reflecting on new insights that will improve course design in the future.