Laggards face looming Windows Server 2003 retirement

Microsoft's ultra-successful server operating system will retire in July -- a deadline many companies will miss

Microsoft Windows Server 2003

Windows Server 2003, Microsoft's first ultra-successful server operating system, will retire in six months, a deadline that many companies will miss, experts said today.

"If it's not broke, don't fix it," said David Mayer, the director of Microsoft Solutions for Insight, a major IT services provider, when asked why Windows Server 2003 has hung on even as its support deadline looms. "It was the first really mainstream server from Microsoft, a really solid OS, and gave Microsoft a lot of credibility [in server software]."

Microsoft will terminate security updates for Server 2003 on July 14, ending the product's support lifecycle. The company launched Server 2003 in April 2000. Like Windows XP, on which it was based, it will have been supported years longer than the usual decade.

Because Microsoft will no longer patch the software after July, companies have been replacing Server 2003 with newer operating systems since the software's peak in 2009, when, according to research firm IDC, nearly 20 million systems ran the OS worldwide.

But there are still millions of machines running Server 2003, with pockets of the software in most data centers, said Jim Vanden Boom, senior manager for software solutions at CDW, a competitor to Insight. And with the support deadline quickly approaching, customers are scrambling.

"Depending on what is running on those servers, it can be a significant effort," Vanden Boom said of replacing Server 2003.

Although Microsoft publishes support deadlines long in advance -- and has been beating the drum to dump Server 2003 for months -- it's not unusual for customers to hang on too long. Last year, as Windows XP neared its final days of support, there were still huge numbers of systems running the aged OS. Companies lined up to pay Microsoft for extended support contracts and PC sales stabilized in part because enterprises bought new replacement machines.

Problems replacing Windows Server 2003 may appear similar at first glance, but they're not: Servers are critical to a business because of the applications that run on them, which may have to be rewritten or replaced. "This is very different from XP," said Vanden Boom. "When a laptop dies, you can just throw away that laptop and get another. The calculus for servers is very different."

"It's a night-and-day difference in complexity," echoed Mayer, when asked to compare Server 2003 migration to that of XP.

"Continued use of Windows Server 2003 is about more than just the OS itself. In the vast majority of the cases, there is an application that is directly responsible for the continued use of older Windows server products," IDC analyst Al Gillen wrote in a recent report on Server 2003 and its impending retirement.

Those applications may themselves be unsupported at this point, the company that built them may be out of business or the in-house development team may have been disbanded. Any of those scenarios would make it difficult or even impossible to update the applications' code to run on a newer version of Windows Server.

Complicating any move is the fact that many of those applications are 32-bit -- and have been kept on Windows Server 2003 for that reason -- and while Windows Server 2012 R2 offers a compatibility mode to run such applications, it's not foolproof.

"Windows Server 2003's end-of-extended-support deadline is really not about an operating system migration/update," said Gillen. "It really is about the entire software ecosystem that remains on Windows Server 2003 today."

It's unlikely that everyone will make the July deadline.

"Most customers understand that some [servers] are not going to make it," said Mayer. "Their best bet is to continue to run [Server 2003] under an extended support model, but before that they should be thinking, 'Let's get that total number down, let's get the easy ones off Windows Server 2003.'"

Microsoft sells after-retirement support contracts, called "Custom Support," to its largest customers, who must have a plan to totally eradicate the unsupported product. Under a Custom Support agreement, Microsoft provides patches only for the security vulnerabilities it has rated "critical," its highest threat ranking.

Because Microsoft charges per system for Custom Support, the fewer Server 2003 systems running at the July cutoff, the less a company will pay.

"But if you have to rewrite apps, that's not going to happen in time," Mayer added.

Vanden Boom's advice was different. "Prioritize," he suggested. "Upgrade those with the most risk to the business first."

Other than a Custom Support contract, neither Mayer or Vanden Boom could recommend a fix for those who won't make the July retirement date, except to press ahead as fast as possible. "We always tell customers to stay in a supported state," said Vanden Boom. Mayer agreed.

Microsoft would like customers facing end of support to shift their servers to the cloud, specifically the Redmond, Wash. company's Azure cloud-based platform.

But while Vanden Boom thought it was still possible for some customers to make both moves in time -- drop Windows Server 2003 and transition those systems to Azure or a competitor, like Amazon's AWS -- Mayer believed it best if companies took a more measured, step-by-step approach.

"Most customers have done it as two separate moves," said Mayer, hinting that it was too much to bite off at once.

This story, "Laggards face looming Windows Server 2003 retirement" was originally published by Computerworld.

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