In this paper, the authors aim to advise IT decision-makers on Windows Server remediation programmes within medium or enterprise sized businesses. Windows Server 2003 has proven to be a dependable, flexible and scalable workhorse, powering companies of all sizes around the globe, across all industries and nations. The lifetime of the operating system has witnessed companies grow in the early 2000s, and then cut back during the recession. These economic and business shifts resulted in large, complex IT infrastructures, which have become unwieldy.