This content is part of the Essential Guide: A guide to Windows Server 2003 end of life
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Solution providers prep customers for Windows Server 2003 end of life

Compared with the Windows XP transition, the migration from Server 2003 may be more laborious and complicated for solution providers. Adding to the challenges, customers' attitudes remain mixed -- despite Microsoft's looming deadline.

It's like déjà vu all over again: Just as companies grappled with the end of Windows XP, the July 14 end-of-life date for all versions of Windows Server 2003 is approaching. With an estimated 20 million Server 2003 machines still in use and no word from Microsoft on whether it will offer extended support, solution providers have no small task ahead of them as they prep customers for a transition.

When mainstream support ends, customers will have a decision to make: update to either Windows Server 2008 or a version of Windows Server 2012, or pay heartily for extended support -- if it's offered by Microsoft as it was when XP reached end of life.

Key business considerations

"I would be surprised if it's less than $1,000 per server," noted David Mayer, practice director of Microsoft solutions at Insight Enterprises, which has called this transition more time-consuming and complex than when support for Windows XP ended.

To get an idea of just how rickety the software is, just think: There were 37 critical updates released for Windows 2003 in 2013, according to Mayer. If a customer opts to do nothing once Microsoft stops issuing security patches and updates, they are taking an incredible risk, he said. "Servers, by their nature, are something you can't unplug, so obviously that's something a customer has to account for. So [unplugging is] an option, but not a real option."

Server 2003 is often loaded on older, legacy-type servers, and when it comes to maintenance and support, it becomes a costly proposition, added Brad Gephart, senior director of the Infrastructure Group at Avanade. There could also be increasing risks for data centers running the outdated software, and businesses will have to deal with added costs for intrusion detection systems, more advanced firewalls and network segmentation, according to Insight Enterprises.

At the same time, he said there is no "one size fits all" approach for moving off Windows Server 2003. If a company has an application running on Windows 2003 that is not business-critical, or it is planning to retire it soon, doing nothing may make sense for certain workloads. However, "Depending on the industry they're in, a lack of … support could be detrimental to their business if they are no longer in compliance," Gephart said. "That's part of the analysis that needs to take place."

Then there are organizations that have "a major necessity" for staying on Windows Server 2003, said Andrew Hertenstein, lead architect of data center and cloud management at En Pointe Technologies. These organizations rely on 32-bit applications that are running on Server 2003. By contrast, most deployments of Windows Server 2008 and Server 2012 are 64-bit. "A lot of times, there's an issue with application compatibility. That's our biggest concern and why [for] a lot of customers, if they still have some 2003 sitting out there, it's usually pretty important that it's kept out there."

Determining a migration path

Solution providers have said the impending Windows Server 2003 end of life has had a mixed reaction among customers so far, ranging from customers who are concerned and want to discuss their options now, to those with an "out of sight, out of mind" attitude. Of course, there are also companies that won't be significantly impacted.

Many enterprise organizations have already moved off Server 2003 because they want to get on newer platforms, have enterprise agreements for stepped-up servers, and prefer to stay up-to-date with technology, Hertenstein said. For organizations that are more budget-constrained, it has been harder to do the upgrade, he said. If they have an application that can't be moved to a newer server version, "a lot of times, organizations have to put a server in the corner and get [the app] on a virtual platform and let that app burn away."

While a lot of organizations were unprepared forXP's end of life and several of En Pointe's larger customers paid for extended support, Hertenstein said he doesn't expect to see as much of that happening with Server 2003. "I think the reason why is it's just not as prevalent in the organization."

At this point, he said, Server 2003's expiration is not a big concern for En Pointe's customers. "We're still nine months out from the expiration date, and it may change in three months when we get closer to the six-month point."

Identifying the apps on these servers and determining the right migration path for them and the various relationships between the apps … is where the complexity lies.
Brad Gephartsenior director of the infrastructure group, Avanade

Mayer agreed. "We really think [that] for customers this is a bit of an unknown" and not a high priority right now, he said. "The majority [of customers] we talk with ... have a general idea of the scope of the issue, but we see customers that don't have a specific grasp" on how certain user communities access their applications and how those servers interact with the rest of their ecosystem.

"Part of the challenge is having a full, solid understanding of the landscape, and that's not always well-known," Gephart said. While it might be easy to determine the number of 2003 instances a company has, understanding the workloads and applications running on top of them are more difficult.

"Identifying the apps on these servers and determining the right migration path for them and the various relationships between the apps … is where the complexity lies," he added. "Often that is not well-understood," because in a lot of cases, apps are turned over to an individual business owner "who doesn't understand the big picture."

Frequently, customers do not keep a list with the names of the applications and servers because each department has their own way of doing inventory and data is often inconsistent across the board. Gephart suggested companies start identifying the customers' servers that run mission-critical apps.

Creating a time table for migration

Insight Enterprises estimates that migration of all systems could take longer than a year to do and recommends companies start a discovery and analysis phase right now to determine which servers and applications are running on the software. Phase two is to execute the migration plan, which could mean software upgrades, hardware upgrades and/or moving to the cloud. The third phase is monitoring to ensure the applications are working well and there is no negative impact, such as downtime.

"The assumption is to move everything to Server 2012, and then, by necessity, we'll backtrack to Server 2008," Mayer said. If an application's vendor is still in business, in all likelihood that vendor has written a 64-bit version of an application, he said. The solution provider can move customers to a supported version of the app. Otherwise, if an application's vendor no longer exists, the application may have to be ported to something else. "Maybe there's a competitor to that app and we can move them to that, and that obviously will require some work, but that's another potential option." The third -- and worst – option, he said, "is there isn't an option, and we have to rewrite the business app in its entirety."

Right now, En Pointe is talking to customers to educate them and create a plan for "application rationalization -- assessing the app to see if it can be updated or put on a new platform," Hertenstein said. En Pointe is also recommending its customers get Server 2003 systems virtualized, if possible, to eliminate the hardware update.

Meanwhile, there are customers that are of the opinion that Microsoft will extend the Windows Server 2003 end-of-life date. Microsoft pushed out the end-of-life deadline for XP at least once, so they are gambling on the assumption that the company will do the same with Server 2003, Mayer said. "Once we see a definitive statement from Microsoft … we think it will definitely accelerate the [migration] process quite a bit. Do I think this will be a shockwave like XP's end of life? No."

Next Steps

Find out the surprises Windows XP end of life served up for partners

Learn more about preparing enterprises for a Server 2003 upgrade

HP calls on partners to drive Windows Server 2003 end-of-life revenue

Dig Deeper on Operating Systems and Software Services

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How much Windows Server 2003 migration business does your company expect to have?
We have finally, just within the last 6 months, finished upgrading our Windows 2003 servers. There were only a few applications that needed to be modified for the upgrade.
We finally completed our upgrades. It was done in-house. We are definitely budget constrained and this is just one of those maintenance items that keeps getting pushed aside until the last minute.