This case describes how a service organization approached the Y2K compliance issue and how a complex decision-making process led to near operational disaster. We will see how software vendor relations can be complicated by vendor viability and technological innovations. Another issue we will explore concerns opportunities for personal growth and expanded responsibility in a small business environment. We will see how turnover creates stresses, particularly in an organization of this size. Changes in focus from developing in-house expertise to more extensive use of outside support will be examined. Finally, we will examine the relationships that exist among the various service suppliers and how data is interchanged between these suppliers and the organization. While standards exist in other fields, none have been adopted here. Case readers will be encouraged to formulate upto- date management strategies that address these issues head-on.