Windows Server 2003 has been a stable and reliable operating system that enterprises have depended on for years, but it\u2019s coming to its end-of-life shortly. Sound familiar? Companies went through a similar experience with a desktop operating system not that long ago. The experiences that enterprises had during that transition provide some valuable lessons for the current one\u2014for which the stakes are even higher.\nAs with Windows XP last year, many organizations are postponing the shift until they can no longer avoid it. Web analytics firm StatCounter found that Windows XP\u2019s global market share was still nearly 19% last February, just a couple of months before its end-of-life.\nFor those companies that were behind the ball during the migration from XP, one singular lesson shines through: The support overhead costs of maintaining legacy platforms after Microsoft ceased providing support were massively detrimental to their business.\nMany companies that postponed Windows XP migrations found increasing software crashes as new applications requested additional operating systems resources. Windows Server 2003 runs 32-bit applications, while the Microsoft-recommended migration path Windows Server 2012 R2 only supports 64-bit applications. That means similar problems can be expected for those enterprises stubborn enough to remain on the legacy system.\nAfter support ceased, Windows XP users increasingly called internal help desks as they experienced more problems with their computers. This lead many companies to allocate additional IT resources toward maintaining desktops and notebooks\u2014often at the expense of enterprise IT initiatives. Internal support costs for maintaining the legacy operating systems increased dramatically. Again, enterprises should expect a similar scenario with Windows Server 2003: a server that is no longer receiving regular software updates and security patches will require increased maintenance and troubleshooting.\nIT can also learn deployment lessons from Windows XP upgrade strategies. User workstations could be gradually migrated based on need without serious or imminent threat to the health of the company, but with server operating systems, the stakes are higher. Enterprise security and compliance are major threats to organizations continuing to use Windows Server 2003 after its support deadline. Those costs won\u2019t just add up\u2014they\u2019ll crush you.\nAccording to Andrew Hertenstein, manager of Microsoft datacenter solutions for En Pointe Technologies, a Microsoft systems integrator, \u201cFor most of the compliance specifications out there, we have to be on a patched server. Well, that goes right out the window the day you stay on 2003 because you won't be patched. You won't be up-to-date. Your security vulnerabilities are still there.\u201d\nThere is a greater imperative to migrate all servers quickly to minimize exposure than with a desktop OS. If IT drags their feet on this migration, it will require additional investment in firewall and intrusion detection system platforms to secure the legacy server infrastructure. This will drive up capital costs as well as the operational costs of managing additional network devices.\nWeaning off successful enterprise software can be a difficult challenge for enterprises that come to depend on reliable, stable operating systems when so many other factors in the IT world are less dependable. If your company is still having trouble justifying the cost or initiating the process for any other reason, perhaps a long hard look at the internal struggles and rewards you faced when upgrading from XP will provide the proper catalyst for migration. Just remember, this time around the risks are greater than ever.\nWith the end of support date for Windows Server 2003 fast approaching, there's never been a better time to plan your data center transformation. Our experts have designed\u00a0this helpful tool to get you started\u00a0on the right upgrade path for your unique environment, applications, and workloads.