This document discusses lessons learned from migrating courses from Blackboard to Sakai at multiple schools at the University of North Carolina. It includes 3 case studies: 1) The School of Public Health migrated fully online courses by replicating Blackboard functionality and organization in Sakai. They encountered minor issues with the editor and linking documents. 2) The School of Government migrated their MPA program to ensure consistency across courses. They developed tools to import content from Blackboard and provided faculty training and support. 3) The School of Medicine aims to extend Sakai use beyond the classroom for projects, websites, calendars and data repurposing. They use it for committees, research groups and hosting open/restricted files.