This content is part of the Essential Guide: A guide to Windows Server 2003 end of life
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Weighing next steps following Windows Server 2003 end-of-life

With Microsoft ending support for Windows Server 2003 in July 2015, upgrading is more complicated than just rolling in the next shiny new server from Redmond.

Upgrade decisions involving Windows Server used to be relatively uncomplicated: When an aging on-premises server began to sag under the growing load of applications and data, most IT shops made a call to Microsoft so they could start evaluating the next version.

But for organizations still running Windows Server 2003 in 2014 -- and some estimate that as many as 12 million machines are running it -- the decision to upgrade has become more complex. More users are well down the road to adopting cloud computing and virtualization, and strategic upgrade alternatives now go well beyond rolling in a newly minted version of Windows Server. Some see the decision as an excuse to revisit plans to usher in a new cloud strategy or reshape an existing one.

"We have converted most servers to [Windows Server] 2008 R2, but there are a healthy number of [Windows Server] 2003 servers hosting older 16-bit apps, ," said an IT professional at a large Texas-based Web services provider. "Only half those servers are virtualized; the rest are on-premises, so it's worth taking a look at what whether we should just upgrade the internal servers to Windows 2008, or do we virtualize everything with Microsoft or someone else?"

Another service provider who deals with a range of midsize and larger corporate shops agrees.

"This is very much an inflection point [for users] in the design, architecture and management of their data centers," said David Mayer, practice director at Insight Enterprises Inc., a technology services provider. "It has opened up conversations about what is the right thing to do for the future involving adoption of SaaS [software as a service] and IaaS [infrastructure as a service] products and services. It is becoming a multipronged conversation talking about a wider set of choices."

Skipping out on Server 2008

Many Windows Server 2003 users are considering skipping over Windows Server 2008 and landing on Windows Server 2012 because Microsoft plans to discontinue mainstream technical support for the 2008 R2 operating system on Jan. 15, 2015. But a move up to 2012 would be significantly more expensive, given the price of the hardware needed to properly run the raft of high-end features not in the 2003 version.

"Windows Server 2012 gives you some great capabilities, but they come with the need for more powerful and expensive hardware. But that hardware also gives you advantages, too. So there are clear pluses and minuses to this decision," Mayer said.

Microsoft, of course, has heavily promoted the idea that Windows Server 2012 is a Web-ready OS with its Azure cloud environment built in, along with its Hyper-V virtualization environment.

But before moving applications and data to Azure, users must first upgrade to Windows Server 2008 R2 or Windows Server 2012 R2, with the latter requiring a significant investment in added hardware and software.

Since Microsoft is ending technical support for Windows Server 2003 in July of next year and many IT shops lack internal support to carry out migrations involving hundreds of servers, they must turn to external experts for help.

"There is no easy path to Azure for 2003 users," said James Strayer, vice president of product management at Racemi, an Atlanta-based cloud migration specialist. "Windows Server 2003 is the bulk of our new platform support requests now. Some of these users sat on it for so long they are stuck. And now they want to migrate to new applications to the cloud and retire old ones."

What complicates matters is that many of the apps that users want to migrate are highly customized or internally developed, a trickier if not more expensive and time-consuming proposition, Strayer added.

The consequences of not transitioning off of Windows Server 2003 by July 2015 could be dire for some enterprises. After that date, Microsoft will no longer issue security updates and other patches, which could put mission-critical applications at risk. Staying on the aging platform also complicates staying in compliance with a range of 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, an analyst at IDC in Framingham, Mass. "Do you want to be the IT guy who tells your CEO the company is not compliant with something like PCI or HIPAA because upper management didn't want to upgrade? This is one of the reasons why upper management should support an upgrade."

Enter cloud stage left

The lack of a migration path to Azure for Windows Server 2003 users has opened the door for competitors such as Amazon and Google to step in and yank away operating system as well as cloud revenues from Microsoft.

Racemi's Strayer, for instance, says he has seen growing interest among Windows Server 2003 users to jump to Amazon Web Services as the deadline for ending technical support looms closer. Racemi's fully automated migration approach appeals to some understaffed IT shops because it gets a Windows Server 2003 instance up and running in a few minutes in the Amazon cloud, he said.

"Amazon does have import tools, but they have limitations for things like multidisk configurations, and generally there is a fair amount of manual effort involved," Strayer said. "You have to take the servers offline, and that doesn't appeal to a lot of enterprise users. We can take a live capture of the server instead, avoiding an impact to services they are offering."

Insight's Mayer also sees some Windows Server 2003 users willing to dip their toes in the Amazon waters, but Microsoft is not out of the picture.

"We see a lot of users making the decision to at least try individual workloads on something like [Amazon Web Services] and Azure. They think it could be time to move to a SaaS model for those workloads that lend themselves more to that platform like Office 365," Mayer said.

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