As eLearning becomes an increasingly common strategy to minimize instructional disruptions caused by illness, weather, professional development, and other planned and unplanned events, teachers need to gain the knowledge and skills necessary to design and facilitate these non-traditional learning experiences. Informed by survey and interview data, we developed three learning modules designed to assist PK-12 teachers in preparing, planning, and facilitating eLearning experiences. In describing this design process, we focus this case on design judgments, described here as the deliberate and unconscious thinking processes experienced by designers in the design and development of learning experiences. Through this experience, we found that design judgments occur constantly throughout the design process and manifest themselves in non-linear and sometimes unpredictable ways. With this focus on design judgments, we aim to provide a view of instructional design that can sensitize designers to the complexities of authentic design experience.Supplementary InformationThe online version contains supplementary material available at 10.1007/s41686-022-00063-3.