Divorcing one student information system and hooking up with another can cause serious upheaval. With the right plan in place, the transition to a new student information system can go surprisingly smoothly. The author interviewed technologists at Southwest Wisconsin Technical College and the Emily Griffith Opportunity School (CO) who recently have endured these changes. The author also polled some SIS experts for transition tips. The author has even chatted with folks from a division of the University of North Carolina-Chapel Hill, where administrators are in the process of implementing a brand-new SIS for the first time. Collectively, the input provides a road map for navigating one of the most difficult undertakings in the world of IT. (Contains 8 online resources.)