“One system for everyone” has been an ideal goal for information technology (IT) management in many large organizations, and the deployment of such systems has been a major trend in corporate world under the name of enterprise systems (ES) (Brown & Vessey, 2003; Davenport, 2000; Markus, Petrie, & Axline, 2000). Benefits from ES use are claimed to be significant and multidimensional, ranging from operational improvements through decision-making enhancement to support for strategic goals (Shang & Seddon, 2002). However, studies (Hanseth & Braa, 2001; Rao, 2000; Robey, Ross, & Boudreau, 2002) of the deployment of ES in private sector organizations show that the ideal is difficult to accomplish. This chapter reports a case in which a major university system in the U.S. attempted to develop an in-house enterprise system. The system is currently used by more than 4,000 individual users in almost 20 universities and state agencies. This case offers a historical analysis of the design, implementation and use of the system from its inception in the mid 1980s to the present. This case indicates that ES design and implementation in higher education are quite challenging and complex due to unique factors in the public sector—including state mandates/requirements, IT leadership/resources, value systems, and decentralized organizational structure among other things—that must be taken into account in planning, designing and implementing ES (Ernst, Katz, & Sack, 1994; Lerner, 1999; McCredie, 2000). This case highlights (1) the challenges and issues in the rationale behind “one system for everyone” and (2) some differences as well as similarities in IT management between the private and public sectors. It offers some unique opportunities to discuss issues, challenges and potential solutions for the deployment of ES in the public arena, particularly in higher education.