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Ended support for Windows Server 2008 leaves clients circumspect

The conclusion of support for Windows Server 2008 has Microsoft partners helping clients decide what to do next. A wholesale transition to Azure is one option under consideration.

It's understandable that organizations haven't immediately parted with Microsoft Windows Server 2008.

Microsoft ended support for Windows Server 2008 in January, forcing organizations to consider making wholesale changes to how they manage and control their technology stacks. But as with any trusted technology, the server operating system has been a reliable backbone since its release more than a decade ago, a timeframe that coincided with enterprises increasingly depending on applications and networks to drive business.

Change is always hard, and a change of this magnitude won't happen overnight, especially when the alternative could mean shifting a large chunk of operations to the cloud, which is what Microsoft hopes for as it promotes its Azure cloud platform as an option. A big embrace of the cloud is a big step for companies that still depend on on-premises mainframes.

"Even though it's the end of life for 2008, many still think it's not necessary to move yet," said Craig McQueen, vice president of innovation for the Toronto-based MSP Softchoice. "Some customers don't want to move too quickly because it's difficult to see the business benefits." And even if a company recognizes they're more susceptible to security risks with Microsoft no longer providing patches and updates to Windows Server 2008, "the life of an IT person is so busy that migration drags on," he said.

Customers weigh Window Server 2008 transitions

Craig McQueenCraig McQueen

McQueen and representatives of three other Microsoft partners didn't offer a number on how many customers have shifted or will soon shift away from Windows Server 2008. But they all said the majority of their customers will, for a little while longer, operate on the side of familiarity.

Many of those customers indicated they will eventually start migrating to Azure or another cloud computing platform, perhaps later this year or next year, but many others still need to make a decision. Microsoft ended support for Windows Server 2008 and 2008 R2 on Jan. 14, coming off the heels of a July 2019 end-of-life date for SQL Server 2008.

Rob LeachRob Leach

Companies that haven't yet committed to halting use of Windows Server 2008 aren't ignorant of security risks, according to Microsoft partners. For every day that passes, they know threat actors increase their efforts to exploit vulnerabilities in the old operating system. "[Windows Server 2008 users] know all about security breaches, and they should do everything necessary to protect themselves. They don't want to be on the front page of The Wall Street Journal," said Rob Leach, the North American Azure lead for the Seattle IT consulting company Avanade.

But the desire to break free of Windows Server 2008 and other mainframe servers is often tempered by contractual and budgetary considerations, Leach said. Many Avanade customers haven't yet entirely shifted to cloud because they are contractually obligated to on-premises servers until those leases expired. But Leach said he expects to see an increase in cloud migrations over the next few years and Azure to be an attractive option because it would be a lift and shift within the Microsoft family.

Even when companies can immediately take advantage of cloud, they nonetheless proceed cautiously, Leach said. Customers want to see specific proof points for how cloud can boost the bottom line over the long haul. "It's not just about technology," he said. "It also has to make good business sense."

David RodriguezDavid Rodriguez

David Rodriguez, the national director of cloud platforms for the consulting firm Core BTS Inc. in Garden City, N.Y., said the effective end of Windows Server 2008 support won't be the sole driving force behind his customers' shift to cloud, but having the end-of-service date "hanging over their heads" will be a factor.

How Microsoft partners can support Azure migrations

Core BTS helps customers overcome any hesitations about cloud, Rodriguez said. "We provide detailed reports with not only a line-by-line breakdown of what each [cloud] service will cost, but also what it will take to reinvest in a new VM host," he said. "We compare side by side the estimated spend if you just upgrade hardware on-premises to what cloud costs." Some are already making the move to a Microsoft cloud, migrating to either Azure VM or Hyper-V, he added.

With an opportunity to sell the benefits of cloud technology, Microsoft partners say they also have a legitimate opening to upsell other services that are related to cloud, including microservices, containers and AI-supported applications.

"The journey to the cloud is crawl, walk and run," Rodriguez said. "With the 'walk' phase … you start to take applications they have in a VM, in the cloud, and look for more platform offerings." For instance, some proprietary applications might work well with containerization. The "run" phase could mean making better use of the data in the cloud by integrating it through a suite of AI applications. "The journey to the cloud can be a complete transformation," he said.

Rory McCawRory McCaw

Rory McCaw, president of enterprise advisory services at Green House Data, a Cheyenne, Wyo., enterprise advisory service, likes to point to client success stories to assuage doubts about cloud migration. One such story centers on an agricultural company in Omaha, Neb., that had relied on mainframe servers, including some usage of Windows Server 2008. The company recently shifted to Azure, on which it built a mobile application that lets its trucking fleet better manage its transport of soybeans, he said.

Still, even though the end of support for Windows Server 2008 is a bridge to cloud, companies will always keep some applications running on premises, McCaw noted. Some applications are so critical and embedded in processes that it sometimes makes sense to leave them alone, at least for now.

McCaw knows some companies that still run Windows 2000 to accommodate those unique apps. "It is firewalled but still going due to the type of application running on it or an inability for it to be modernized," he said. In some instances, he added, the critical application was built internally, but its creators have since left the company and took their knowledge of the program with them.

Determining what migrates and what stays is part of Microsoft partners' migration plans for their customers. Executives don't anticipate problems migrating from Windows Server 2008 as long as the planning process is thorough and the client's goals are considered. "It's really just about trying to understand what they want to accomplish," McCaw said. "It's collecting as much information as possible, and not [really] selling anyone … anything, but instead presenting them with ideas they haven't considered … [so] they can then decide with their knowledge of their own business."

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