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Server 2008 R2 end of life hitting home for many in IT

As Microsoft support for Server 2008 R2 nears its sunset, a raft of complications make it difficult for many in IT to get on board with the Azure platform.

The end of the road for Windows Server 2008 and 2008 R2 is rapidly approaching, but the migration path is not so clear for many in IT.

The Windows Server 2008 R2 end of life is January 2020. Microsoft is using this deadline to make a move to its Azure cloud platform seem more attractive, but many on-premises workloads currently in the data center might stay there for the foreseeable future.

Windows Server 2008 R2, by the numbers

Server OS market share numbers are notoriously difficult to come by, but a January 2018 tweet from Ned Pyle, principal program manager in the Windows Server high availability and storage group, indicated Windows Server made up about 70% of server OS installations with approximately 40% of that number on Server 2008/2008 R2. A recent webinar from the Docker container platform company showed, out of 21 million enterprise applications, 80% of them run on Windows Server, with 70% of that number using Windows Server 2008 or an earlier version.  

Why are the numbers for a server OS that's about to lose security updates still alarmingly high? Because inertia remains one of the most powerful forces in IT. Once IT pays for the Windows Server license and the application runs reasonably well, there is strong motivation to leave well enough alone. Microsoft wants Windows shops to move these 2008/2008 R2 workloads into Azure with a few enticements. As part of this campaign, Microsoft offers three years of free support for VMs on those OSes after the Windows Server 2008 R2 end-of-life date. Microsoft will give extended support after the January deadline for companies with deeper pockets that can afford the extended security plan.

"This is an opportunity for Microsoft to get people either into Azure or into a sort of hybrid mode, which is not just a stick-your-head-in-the-mud strategy anymore," said John Abbott, analyst with 451 Research. "You can actually get some value of having some on-prem connected to the cloud. People are starting to realize that for the first time."

When it comes to Windows Server migrations, pick your poison

Despite Microsoft's siren call for Windows shops to make their lives easier and put those 2008 R2 workloads into Azure, it's not a simple process. For better or worse, Windows Server is tightly integrated with the day-to-day operations of many organizations and handles a wide range of responsibilities, so any change is likely to cause some form of disruption. Even organizations that rely on a cloud service, such as file sharing, most likely use on-premises Active Directory to handle the single-sign on process so end users only need one set of credentials to access the SaaS applications and services .

This is an opportunity for Microsoft to get people either into Azure or into a sort of hybrid mode, which is not just a stick-your-head-in-the-mud strategy anymore.
John Abbott Analyst, 451 Research

For organizations that want to stay on premises and migrate to a newer Windows Server OS, that operation is not much easier. If the decision is to move to Windows Server 2016 or 2019, then it requires a double hop: first to Windows Server 2012, then to the desired server OS. For some, it might be enough to move to Server 2012 R2 to stave off the loss of security updates, but that server OS leaves extended support in October 2023.

"For years, Microsoft didn't really take into account these sort of problems," Abbott said. "Now, it is starting to look at the rest of the industry and say, ‘We really do need to support some of these older versions and move them up.'"

Windows Server 2019 introduced a Storage Migration Service feature, but as the name indicates, it only handles storage roles, not applications. The Windows Server In-place Upgrade feature, which preserves features and settings for a deployment while transitioning to a newer Windows Server version, only works for two previous versions.

Not only are there are a number of technical hurdles related to a server OS migration, but there are logistical problems to unwind. For example, if a company has a single 2008 R2 installation but that server runs multiple roles -- Active Directory, print server and domain name services -- trying to avoid downtime might be next to impossible.

IT's dirty little secret is there are still plenty of applications running on unsupported Windows versions. In quite a few instances, the reason is to keep a legacy enterprise application running. Ned Pyle's tweet thread mentioned that about 15% of Windows Server workloads were on Server 2003, which went out of support in July 2015. Despite the real threat of ransomware and damage to the corporate brand, many organizations continue to fall victim to these threats. The 2017 WannaCry outbreak is one example of attacks that used vulnerabilities in outdated Windows systems to lock up data and hold it hostage.

For some, it's a question of too much cloud

Michael Stump, a systems engineer who handles infrastructure hosting for a US federal agency, works in a traditional operational environment, managing a mix of VMware, SQL, SharePoint, Solaris, Linux and storage workloads.

For Windows Server, he estimated about 10% are on Server 2016, 50% to 60% are on Server 2012 R2 with the remainder on Server 2008 R2. There are several Server 2008 workloads that are hanging on due to application requirements. With approximately 500 workloads total on Server 2008/2008 R2, Stump said migrations to another on-premises Windows Server OS will be the main focus of his environment this year, but most likely not Windows Server 2019.

"A few of us are interested in [Server 2019], but because there's no compelling reason for us to move to it at this time, we'll probably lag for a couple of years on that one," Stump said. "There's a lot of hybrid cloud technologies and migration technology built in 2019 that I think is really just a Trojan horse to get you into Azure. We're just not there yet."

Stump is not averse to the cloud. He already works with a number of cloud vendors, but he wants to avoid adding more to the mix.

"I think the only one we haven't collected yet is VMware AWS, but they're eagerly trying to push us in that direction. I don't want to end up with too many clouds," he said.

While 2018 was a turbulent one for Windows administrators -- he dubbed it "the year of the rescinded patch" -- Stump said Windows Server is a solid operating system, and part of the blame for bad experiences with patch deployment falls on the administrator.

"I don't want to blame the victim, because ultimately Microsoft made a bad patch, but if the administrator is not applying any analysis to the Microsoft patch, then the administrator could literally be replaced with a scheduled task and a PowerShell script," Stump said.

Surveys show healthy interest in remaining on premises

Results from the TechTarget IT Priorities Survey for 2019 indicated that while just 19% of organizations plan to increase spending for stand-alone x86 servers, interest in hyper-converged and converged infrastructure is strong with 69% and 54% of organizations planning to spend more in those areas, respectively. Those results, coupled with a strong interest in spending in PaaS and IaaS seem to indicate a thawing attitude toward cloud services and hybrid cloud deployments in the enterprise.

This matches up with what Abbott sees from a recent 451 Research survey in which about 30% of companies expected to increase the number of x86 servers in 2019. He said one reason for this growth could be to establish a hybrid cloud in these organizations.

"This isn't just laggards continuing to stick to on-prem because they're frightened of going to the cloud. It's more that they are looking to do things like hyper-converged composable and open converged infrastructure," Abbott said.  

He said Microsoft appears to recognize these growing cloud ambitions with the enhanced and new features in the Windows Server 2019 release, such as cross-domain failover clustering and support for Kubernetes container orchestration.  

"The hybrid cloud support with Azure and the software-defined networking makes it easier to run multi-cloud. Microsoft's actually adding features that Linux and Azure people have had for some time, so that's I think that's encouraging," Abbott said.

This was last published in March 2019

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After the Server 2008 R2 end-of-support date, will you put those workloads on a new Windows Server version or move to the cloud?
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