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Why breaking up with Windows Server 2003 is hard to do

With end of life looming for Windows Server 2003, more users are migrating to Windows Server 2012. But for some it is taking longer than expected.

As Windows Server 2003 approaches end of life, more IT shops are migrating to modern versions of the platform, most notably Windows Server 2012. But the decision isn't so easy, or so obvious.

The not so easy part has to do with overall migration costs that include significant hardware upgrades, updating mission critical, off-the-shelf and internally developed 16- and 32-bit applications to exploit 64-bit operating system environments.

The not so obvious part has to do with classic corporate inertia or outdated thinking about what it takes to keep an IT organization competitive in the new era. An education in modern datacenter technologies rather than an expanded IT budget can better remedy the latter, according to some.

"An enterprise user called me wanting to upgrade from [Microsoft's] .Net 1.1 to 4.5 and was using Windows Server 2000. I told them going to [.Net] 4.5 was the least of his problems," said Mike Drips, a solutions architect with WiPro, Inc. in Houston." There are more than a few of these companies out there who continue to live by the old adage: if it ain't broke, don't fix it. That approach works until it doesn't."

While it is hard to get an accurate number on how many Windows Server 2003-based servers are in operation today, most analysts feel comfortable estimating in the neighborhood of 10 million.

 "I do find it astonishing that so many companies suffer from this level of inertia," said Michael Cobb, an independent IT consultant. "The example I use is that of a Formula 1 team, who are already developing next year's car even though the current Formula 1 season isn't over. IT department's need more of this mentality."

Inertia aside, most organizations have delayed migrating because their budgets can't accommodate the purchase of either new hardware and software platforms and/or refurbishing old, but critical, internal applications.

Some shops however, will spend the money but only on those applications that are the primary drivers of revenue growth.

"This transition is all about the switching costs," said Vic Nyman, COO and co-founder of Blue Stripe Software, which specializes in monitoring and fixing distributed applications. "Dealing with these corporations, we see the applications driving their business model and revenues are all on the latest version of Windows Server. But for things like email and internal routing software, more often than not they are on older platforms like Windows Server 2003."

Windows Server 2003 nears end of life

The consequences of sticking with Windows Server 2003 after July14, 2015, when Extended Support ends, could be dire for some shops. After that date, Microsoft will no longer make available security updates and other patches, which could put mission critical applications at risk.

Staying on the aging platform also complicates compliance with a range of different federal and state regulations.

"The end-of-life for a server-side product presents much greater problems with things like regulatory compliance," said Al Gillen, program vice president, servers and system Software with IDC in Framingham, Massachusetts. "Do you want to be the IT guy who tells your CEO the company is not compliant with something like PCI or HIPPA because upper management didn't want to upgrade? This is one of the reasons why upper management should support an upgrade."

But server OS migrations are  a bit more complex than migrating off desktop operating systems such as Windows XP.

Gillen and others agree that the inability to get rid of 16-bit applications is a major issue, particularly among cash-strapped, mid-size organizations that can't afford the required computing platforms, or to hire the talent to rewrite the applications.

IT shops are also reluctant because upgrading essential applications such as antivirus, agent management and other software that touch the kernel can be tricky, and will likely "break" in a migration. Beginning with Windows Server 2008 R2 in 2009, all versions of the operating system are fully 64-bit.

"Architecting a successful transition will cost you time and, if you don't have the talent in-house, the money necessary to hire good people," Drips said. "But people that wait this long don't like to spend and do things on the cheap, and that can be an even costlier way to go."

What makes the hardware particularly expensive is that many Windows Server 2003 shops skip Windows Server 2008 R2 and go straight to Windows Server 2012. The latter is a much more code intensive operating system with sophisticated environments built in such as Hyper-V, Windows Azure and an assortment of other virtual capabilities.

"The users we deal with going from [Windows Server] 2003 to 2012 are typically going from single image to multi-image VMs," Blue Stripe's Nyman said. "The machines they are buying now are not two-way or four-way boxes, they are 16-way with at least 16 gigs of memory and they are going to higher density virtualization."

The other reason shops bypass Windows Server 2008 R2 is mainstream technical support for that operating system ends in 2015, although extended support goes until 2020. Some users don't want to deal with the worry of technical support ending for their operating system just as they are launching new applications

"More users are telling us they don't see moving to [Windows Server] 2008 as very viable because it is going out of mainstream support next year," said one Microsoft insider. "They want to get the longest possible support cycle out of whatever they buy, but then they have to deal with the hardware expenses. But paying now instead of later could be a better decision."

Transitioning off Windows Server 2003 is a relatively small problem compared to what the Windows Server community faces transitioning off Windows Server 2008. Not only is the Windows Server 2008 user base significantly larger than its predecessor, but there is much more virtualization built into 2008 R2 that has taken deep root in larger corporate environments, according to Gillen.

"The end of life for [Windows Server] 2008 will be a much bigger problem," Gillen said. "For some, it will prove really hard to rid of all the stuff users have it tied to."

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