This paper presents a detailed account of a private US college’s efforts to modernize its directory services, email, and calendar systems across faculty, staff, and students. Written from a first-person perspective, the paper takes the reader through an intimate retrospective description of the key decisions, timeline, challenges, outcomes, and lessons learned for each of the three separate migration projects over a three-year period. The author has included sufficient detail to allow readers with technical knowledge to appreciate the nuances and intricacies of the obstacles she encountered and how she overcame them.

However, the resulting lessons are not necessarily directly transferable as a road map for migrations undertaken elsewhere. User requirements vary substantially and system capabilities and limitations evolve too quickly to ever permit a one-size-fits-all template for migration projects. Instead, the paper contributes to a collective body of wisdom that increases awareness of caveats and best practices, which is sure to benefit any project team involved in such an endeavor.