This content is part of the Essential Guide: A guide to Windows Server 2003 end of life
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Get your Windows Server 2003 migration underway -- or pay

Windows Server 2003 migrations are not for rookie IT admins, but the cost of delaying a move is even more overwhelming.

IT shops still on Windows Server 2003 will lose service in less than six months, and must either migrate to a newer platform or pay Microsoft's exorbitant extended support fees.

"We always stress that if you haven't even started and don't have a plan B, reach out to Microsoft to learn what the extended support fee will be, and that will probably spur action," said David Mayer, practice director, Microsoft Solutions for Insight Enterprises, Inc., an IT service provider which formed a “Rapid Response Team” to help businesses migrate off Windows Server 2003.

Custom support agreements (CSA) will be available for enterprise customers that may have a large volume of servers and cannot finish the migration by July 15, 2015. Costs can vary depending on specific customer needs, such as the number of instances requiring continued support, a Microsoft spokesperson said.

CSAs generally run around $600 per server in year one -- that's more than the $565 a Windows Server 2003 license cost large customers back in 2003, according to Paul DeGroot, principal consultant with the independent Microsoft licensing consultancy Pica Communications in Camano Island, Wash.

If you had, say, 5,000 [Windows Server 2003 licenses] …you're going to spend $21 million on this over the next three years.
Paul DeGroot consultant, Pica Communications

For a customer with 1,000 Windows 2003 servers -- and there are enterprises with multiples of that -- custom support bills could add up to $600,000 in the first year, $1.2 million in year two, and $2.4 million in year three, DeGroot said.

"If you had, say, 5,000 of these -- and that happens -- you're going to spend $21 million on this over the next three years," he said.

Pica Communications has a number of enterprise clients that still run Windows Server 2003, because it was a stable operating system and IT pros fear applications will break during an upgrade.

"So after paying Microsoft millions for a few years of grace…they'll pay millions more to rewrite or replace the apps with something new that, hopefully, will continue to do what it did back in 2003," DeGroot said. "A lot of dough just to keep doing what works fine today."

One less expensive strategy is to use a CSA contract for the first year, when it's cheap and the odds of getting a patch are a bit better, and switch to Custom Support Essentials after that, because companies pay only for the servers on which the patch is deployed, DeGroot said.

"This is nice since a lot of patches are critical only for some special combination of configuration, software, and hardware," DeGroot said.

In 2014, Microsoft issued 25 Windows Server 2003 patches. So while some IT pros may be tempted to let support lapse, it's a gamble not worth losing, Mayer said.

"We would never encourage people to go completely unsupported," Mayer said. "You are opening yourself up to issues."

There are plenty of companies who may be in that position today. Microsoft claims there are about 20 million Windows Server 2003 units in the ecosystem today.

Rory McCaw, CEO, Infront Consulting Group, Inc., a Las Vegas-based firm that helps enterprises migrate to newer versions of Windows, said more than 80% of his customers still have Windows Server 2003 in their environment. Of them, the majority of projects are underway, especially for compliance-regulated apps.

Many have delayed the upgrade because Windows Server 2003 works fine -- and platform upgrades are about as fun as a visit to the dentist.

"There is a level of hangover from the Windows XP upgrade process, and for large organizations that was, and continues to be, a painful process," Mayer said.

The Windows XP deadline was moved, so some IT shops hope the same will happen with Windows Server 2003 -- but it's not likely, Mayer said.

Windows Server 2003 migrations lead to Windows Server 2012, Azure

While some companies that have standardized on Windows Server 2008 move to that version, most jump to Windows Server 2012, Mayer said.

In TechTarget's 2015 IT Priorities Survey of 2,212 IT workers across the globe, 39% of North American respondents and 30% of respondents globally said an upgrade to Windows Server 2012 is among their major projects for the year.

Companies on Windows Server 2003 that want to re-write their apps for mobile users should either move to a cloud service or Windows Server 2012 R2, which is a stepping stone to cloud, said Scott Woodgate, director of product marketing on Microsoft's cloud and enterprise team.

"Web apps are great for the cloud, particularly because the cloud has 19 regions and scalability that on-premises [servers] do not," Woodgate said.

But a move to the cloud certainly isn't for everyone, Infront Consulting Group's McCaw said.

Microsoft suggests taking these steps to begin a Windows Server 2003 migration

  1. Discover and catalog all of the software and workloads running on WS03. Tools such as the MAP Toolkit can help, along with third-party products from companies like, Avanade, Citrix, Dell, HP, AppZero, Lakeside Software and Nimbo. Partners can be found via Microsoft Migration Planning Assistant.
  2. Assess what you have by categorizing and analyzing apps based on type, criticality, complexity and risk.
  3. Target your destination for each app and workload. Options include Windows Server 2012 R2, Microsoft Azure, a hosting service provider and Office 365.
  4. Migrate. Customers not looking at cloud options need to factor in hardware upgrades.

"Not everyone is looking for business transformation," McCaw said. "They just want to run as efficiently as possible, and for many people that means staying with on-premises servers that they know. There is less of a learning curve."

The majority of Windows Server 2003 migrations lead to on-premises systems, Microsoft said.

IT integrators agreed.

"We are not seeing moves from on-prem to the cloud," Mayer said. "People generally move to [Windows Server] 2012, and then they are in a better position to move to the cloud from there, once they are modern and stable."

Windows Server 2003 migrations not for rookies

IT shops who have put off Windows Server 2003 migrations didn't expect the move to be as difficult as it is, Mayer said.

"You can't just move to Windows Server 2008, or 2012, because of the architecture change," he said. "We generally see that about 25% of the physical servers have to be replaced with modern equipment."

IT consultants can help companies start or finalize documentation and inventory data, and map that to their business processes to categorize servers from difficult to easy, based on workloads, Mayer said. The migration timeline depends on factors such as whether there is a 64-bit version of an application, or if an application vendor has gone out of business, he said.

There are some migration tools to help speed the integration process along, such as the free Microsoft Assessment and Planning (MAP) tool, or third-party tools from companies such as AppZero Inc. and Zynstra Ltd.

"These assist, but the tools are in no way a silver bullet," Mayer said. "It doesn't do all the logistical exercises that are necessary."

Bridget Botelho is senior news director for data center and end user computing media groups at TechTarget. Contact her at [email protected] and follow her on Twitter @BridgetBotelho.

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