This case study reflects on a long-term collaborative partnership between librarians and writing program administrators to plan, build, implement, and significantly revise two course-specific online learning modules. Of particular interest are contrasts between phase-delineated instructional systems design frameworks, such as ADDIE, and the often recursive, unpredictable, and messy paths of project development in practice. In describing the evolving uses of the modules within an ecosystem of programmatic library instruction, this study also demonstrates the utility of flexible, iterative, and organic approaches in evaluating, revising, and repurposing instructional design projects to meet unforeseen challenges and opportunities in an academic libraries context.