In order to keep on the leading edge of technology and to take advantage of new administrative features, we at University of Wyoming decided to upgrade our Windows NT 4.0 lab system to a Windows 2000 based lab system. This paper will detail the planning that went into this project and the numerous issues that were faced. Some of the planning topics that we will discuss are: • Hardware requirements and the need to upgrade machines • Software testing and the need to find updated versions, or replace legacy programs • Political ramifications of such a campus-wide upgrade • Developing a workable time-line for the upgrade process In addition to detailing the planning process of the upgrade, we will also discuss some of the problems and issues encountered during the first stages of the upgrade process. Keywords Windows 2000, upgrade, lab system, operating systems