This document outlines Northern Illinois University's plan for upgrading their learning management system from the current Blackboard version to the next generation version. The plan involves 5 phases: 1) preparing documentation and support materials, 2) communicating new features to users, 3) preview sessions for faculty, 4) hands-on workshops over the summer, and 5) open labs and special sessions after the upgrade. Over 40 workshops and information sessions are scheduled on campus and online. The challenges will be updating all support materials for the new version and providing training to over 1,300 faculty during the summer months. Technical considerations around storage, building blocks, and timing of the upgrade outage will also need to be addressed.