Despite the increase in formats of online education, evidence suggests that the academic achievement gap could widen without iterative adaptation. This comparative case study analyzes the implementation of an online undergraduate course delivered consecutively in hybrid and fully online formats. Student feedback and instructor reflection address adaptive processes for online learning and adjustments to enhance the second course following a sequential redesign. Results include students' challenges with technology and workload, benefits of cross-course collaboration, instructor efforts to mediate challenges without sacrificing rigor, and advice for educational developers as they support online teaching through rapid adaptation by design.