Time to Say Goodbye to Windows Server 2003: Preparing for Migration (Part 1)

If you would like to read the next part of this article series please go to Time to Say Goodbye to Windows Server 2003 – Preparing for Migration (Part 2).


It happened to Windows XP, and now Windows Server 2003’s day is coming. On July 14, 2015, Microsoft will be ending support for the popular server operating system that is still running on many corporate and public sector networks despite the fact that it is over a decade old and (if you count the R2 versions) four versions behind. If your company is one of those, it’s time to start planning for the migration that should be completed less than a year from now.

In IT we’re often focused on putting out today’s fires and reviewing yesterday’s mistakes, and don’t devote enough time and energy to planning for tomorrow. It might seem as though you still have plenty of time, but in reality the months pass very quickly in our fast-paced world, so if you don’t already have a plan in place, you should start designing one sooner rather than later.

In this article, we’ll look at some of things that made Windows Server 2003 great in its day, and why (in addition to the impending lack of support and cessation of security updates) it’s time to move on now. Then we’ll walk through the process of developing a migration strategy that best fits your particular organization and how you can use the tools Microsoft has provided to help make the transition a little easier.

That was then; this is now

Windows Server 2003 was introduced in April of 2003, more than eleven years ago. Its latest major update was Service Pack 2, which was released in March of 2007, about seven years ago. Server 2003 replaced Windows Server 2000, which was the first of the post-Windows NT server operating systems from Microsoft.

WS2003 added many improvements over its predecessor(s), including improvements to Active Directory and Group Policy, easier upgrade/migration from NT, better disk management, backup, and scripting tools and a whole new version of IIS. Service packs 1 and 2 increased security, added new management tools and made many improvements to networking support (IPv6, WPA2, etc.).

WS2003 was the right OS for the job at the time, but the job has changed. Today’s networks are very different from those of ten years ago. With the advent of big data, the mobile revolution, the cloud, and far more sophisticated security threats, WS2003 is no longer up to the challenge. As your organization moves ahead into the future, your network infrastructure can’t stand still. The upcoming end of the support lifecycle provides the perfect impetus to take a look at the changes in the way your business operates and evaluates how your network needs to change, then prepare to take the necessary steps to get it there.

Once upon a time not so long ago, the path forward was pretty easy to figure out, albeit not always easy to implement. Today, it’s not so clear. You have more choices – and choice is a good thing, but also makes your job a little more difficult. Let’s look at what some of those choices are.

Migration options

WS2000’s approaching demise comes at a time when the very nature of networking is in transition. Similar to the paradigm change that occurred when organizations began to move from a mainframe-based computing model to a peer-to-peer and then client-server model, we’re now starting to move from an on-premises datacenter model to a cloud-incorporated model. But while the cloud is almost certain to play a role in your company’s networking over the next decade, there are several different ways in which it can do so:

  • You can stick with the traditional datacenter where the vast majority of your resources remain on company premises, while perhaps utilizing web apps and other cloud services as secondary resources. This will be favored by more conservative organizations that aren’t ready for a whole new way of doing things.
  • You can migrate to a private cloud, using the same technologies that cloud service providers use and following the essential guidelines for cloud computing, but keeping the cloud on premises. This will be favored by organizations that want to benefit from the characteristics of cloud services (such as on-demand self-service, resource pooling, measured service, etc.) but that deal with a great deal of highly sensitive data that they don’t want to trust to outside cloud providers.
  • You can migrate everything to a public cloud, where the vast majority of your resources reside off premises in the provider’s secure datacenter, including data storage and application hosting, and the provider takes care of such mundane tasks as updating your operating systems and applications and ensuring that proper security mechanisms are in place. This is an especially attractive option for small and mid-sized businesses that may not have the budget for a fully staffed IT department.
  • You can deploy a hybrid cloud infrastructure, with some of your resources staying on premises and others entrusted to cloud providers. For instance, you might decommission your on-premises email and public web servers and switch to Office 365 for those services, but keep your file storage and intranet servers on premises. This is a “best of both worlds” choice that works well for organizations that want as much of the convenience of public cloud services as possible but have some functions or data that they are more comfortable with keeping under their complete control.

Your choice of future computing infrastructure models will determine how you will migrate from WS2003, as well as which computers will be upgraded (both in terms of operating system and, most likely, hardware) and which will be removed and not replaced. You might find that you’ll be able to drastically reduce the physical footprint of your datacenter if you decide to go with a more cloud-centric model, or you might discover that you need to buy a great deal of new hardware if you stay with the traditional datacenter or a private cloud model (keeping in mind, however, that private cloud, like all cloud computing, is very virtual machine-centric so you may need to plan for fewer – but more powerful – machines).

Cost factors

One reason organizations put off upgrading is a practical one: the outlay for new operating system licenses can be substantial, but there are of course other costs that may flow from that. Your old hardware may not be able to effectively support the new OS, so you may need to upgrade it at the same time. You may also find that some of your applications won’t run on the newer OS and you’ll have to upgrade them to newer versions, as well. Custom line-of-business applications may have to be modified and if you’re in the position of many organizations, where the company that created the custom app for you is out of business, you might have to find a substitute, which can involve considerable expense in administrative overhead, testing possibilities, lost productivity and learning curve for users.

It’s important to remember, though, that the cost of operating WS2003 will increase after support ends. You’ll have to enforce more external security mechanisms in order to meet any compliance requirements (if in fact you’re able to meet them at all with the old OS). Cost of administrative overhead is likely to increase. And the potential for a much greater cost exists, if a security breach attributable to “zero day forever” exploits on the unsupported OS should occur. Ponemon Institute estimates the average cost of a data security breach for a U.S. company to be $3.5 million in 2014.

Despite the initial outlays, there are potential cost savings associated with upgrading your network, whether the path you choose is to keep the traditional datacenter model and upgrade your servers to Windows Server 2012 R2, put everything into the cloud, or something in between.

A Forrester Total Economic Impact (TEI) study commissioned by Microsoft examined the potential return on investment (ROI) that enterprises with current volume licenses may realize by upgrading to Windows Server 2012 R2 with System Center 2012 R2 and found that upgrading helped to reduce management costs, storage hardware costs and licensing costs, and that it also made cloud integration less costly

Cloud computing, on the other hand, can significantly reduce energy costs – a big expense for large IT departments, with one study indicating that by 2020, total energy savings for U.S. companies using cloud computing is estimated to total $12.3 billion.

Cloud computing also reduces equipment and staffing costs, as well as the amount of physical space needed for that hardware and personnel. Properly implemented, cloud computing can also increase productivity by providing businesses access to more sophisticated applications and tools at a lower cost. Additionally, the up-front cost of moving to cloud services is likely to be much lower than that of replacing old hardware, operating systems and possibly applications with new.


In this, Part 1 of our series on saying goodbye to Server 2003, we looked at the “why” and started our discussion of the “how” by briefly outlining the options for organizations faced with the prospect of end-of-life of the operating system on which their networks depend. In Part 2, we’ll delve more deeply into that “how,” discussing in detail how to plan for an upgrade of your datacenter to Windows Server 2012 R2.

If you would like to read the next part of this article series please go to Time to Say Goodbye to Windows Server 2003 – Preparing for Migration (Part 2).

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