Microsoft will end extended support for Windows Server 2003 on July 14, 2015, after ending standard support for the operating system (OS) in 2010. As a result, enterprises running critical applications in this environment are at risk. This Technology Spotlight discusses the challenges organizations face in migrating off Windows Server 2003 and key considerations and steps involved in this important strategic IT undertaking. After describing key strategies for migrating the OS and what to look for in a services provider, this Technology Spotlight also reviews HP's service offering for Windows Server 2003 migration.