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Windows Server 2008 End of Life: Risks and Opportunities

Cloud | Posted on June 10, 2019

Inertia is a powerful force, such that Albert Einstein famously said, “Nothing happens until something moves.”

For organizations that have long relied on Microsoft Windows Server 2008 R2, it’s time to start thinking about moving (possibly to Azure) before Server 2008 R2 reaches end-of-life in January 2020 and its extended support finally ends. 

Windows Server 2008 End of Life

The state of Windows Server 2008 R2 on the eve of its EOL

Despite its age, this version of Windows Server remains a key cog of modern IT machinery. Docker has estimated that 70 percent of all enterprise apps run on Server 2008 R2 or earlier. A Spiceworks survey found similar results, with Server 2008 having a larger market share than Server 2012, Server 2003 and all non-Red Hat Linux combined.

Older releases of Windows Server are so embedded in IT operations that they often support SaaS services via on-prem Active Directory for SSO. 

The ongoing centrality of Windows Server 2008 R2 – its inertia – makes any migration a potentially daunting prospect. At the same time, standing pat is not a practical option, either, due to the well-documented risks of relying on outdated and unsupported software, among them:

Options for Windows Server 2008 End of Life

Security risks

Older software is more vulnerable to exploitation, since it doesn’t receive critical patches and in turn becomes a magnet for cyberattacks. The much-covered EOLs of Windows XP and Server 2003 brought some of the associated dangers to light, and the same general issues apply to Server 2008 R2. More recently, the outbreak of the WannaCry ransomware in 2017 demonstrated the real-world cost of keeping legacy apps and the unsupported infrastructure that supports them in place. WannaCry infected hundreds of thousands of computers across 150 countries, causing at least $4 billion in damages


Windows Server 2008 R2 was built for a different world, and as such, it’s missing many features included in its successors. Microsoft has published a helpful chart highlighting some of the functions missing from Server 2008, including Azure network adaptor support, unified management in Windows Admin Center and enhanced Windows Defender Advanced Threat Protection. While not all of them will be needed in every environment, not having access to new features raises the risk of eventually falling behind competitors or suffering unforeseen technical, financial and logistical hurdles.


Like an old pair of shoes, Window Server 2008 R2’s repair and maintenance costs can be costly enough to merit simply purchasing a new replacement. Its total cost of ownership can quickly escalate due to customized security measures, on top of the overhead of poor performance and various incompatibilities with line-of-business applications. Nevertheless, legacy versions of Windows are ubiquitous, due to multiple obstacles en route to modernizing IT environments and the reticence to tinker with operations that more or less seem to be working well.


Evaluating the different migration options for Windows Server 2008 R2

As organizations confront these realities, they have two main possible tracks to take toward an upgrade: Upgrading their on-prem implementation of Windows Server or moving to Azure. Both come with their own set of challenges.

Windows Server 2008 R2 end of life options

Going from Server 2008 R2 to Server 2019 or 2016

If a Window Server environment needs to remain on-premises but be modernized, a multi-phase upgrade is required. For example, going from Server 2008 R2 to either Server 2016 or Server 2019 requires first upgrading to Server 2012 R2. 

Of course, there is the option to simply stop at Server 2012 to reduce the complexity and shorten the overall timeline of the upgrade cycle. After all, Server 2012 is still receiving security updates and its end-of-life is not imminent. But its EOL date isn’t as far away as it might seem. Come 2023, the same challenge now in front of Server 2008 R2 environments will also face Server 2012 installations. 

Microsoft has also pointed out a few key limitations to keep in mind during the Server 2012 R2 phase of the Server 2008 R2 upgrade journey:

  • First, it isn’t possible to perform an in-place upgrade from a 32-bit to a 64-bit architecture, to go from one build type to a different one or to change the language of the installation. 
  • Second, you cannot move from a Server 2008 R2 server core installation to Server 2012 R2 with Server With Full Desktop, i.e., the Server GUI. If you want to make this switch, you can only do so on Server 2012 R2, as Server 2016 and later do not support it.

Such complications can quickly add up. Plus, it might be difficult to avoid costly downtime during an upgrade, especially if a single implementation is supporting multiple functions across an organization. 

With on-prem and hosted environments, there is also the practical need to buy Extended Security Updates from either Microsoft or a licensing partner. These annual update packages became available on Mar. 1, 2019 to customers running Windows Server “under licenses with active Software Assurance under an Enterprise Agreement (EA), Enterprise Subscription Agreement (EAS), or a Server & Cloud Enrollment (SCE).”

Windows Server 2008 upgrade options

Migrating to Microsoft Azure and possibly using a hybrid cloud

Microsoft has provided significant incentives for Server 2008 R2 customers to move their workloads into the Azure cloud. For starters, porting them to Azure IaaS virtual machines as-is is free and comes with three years of free Extended Security Updates beyond the Server 2008 R2 end-of-life at no extra cost. A lift and shift move into Azure is also much more economical in most cases than trying to migrate to AWS or deal with the unpredictable costs of managing an on-prem or hosted environment.

Newer versions of Windows Server also make it more feasible to maintain a hybrid environment. Windows Admin Center within Windows Server 2019 is perhaps the best example, as it provides a graphical interface for managing both on-prem and cloud servers. 

Hybrid Cloud Solutions with Azure

It works with platforms going all the way back to Server 2008 R2, but requires Server 2019 for integration with key Azure services such as Azure Backup and Azure Site Recovery. Backing up on-prem workloads from Server 2019 to the cloud can be as straightforward as using Windows Admin Center in tandem with an Azure account. Other relevant features in Server 2019 include support for Kubernetes orchestration and cross-domain failover.

Together, these capabilities allow for more streamlined hybrid and multi-cloud setups, through which organizations can harness some of Azure’s power while still maintaining an on-prem foothold. Several recent surveys have indicated a growing affinity for this approach, with more than half of respondents to the 2019 TechTarget IT Priorities Survey saying they were interested in converged and hyper-converged infrastructure, despite only 19 percent stating their intent to purchase more x86 servers.

Microsoft’s own assessment from 2018 found that two-thirds of the IT professionals it surveyed were on hybrid cloud and that more than half of them had moved to it within the past two years. Data storage, backup, and recovery were the top use cases for hybrid cloud. 


How to approach Windows Server 2008 R2 EOL

The best way out of Windows Server 2008 R2’s end-of-life phase will depend on your requirements. Whether you decide to remain in an on-prem/hosted environment, make the move to Azure or decide to configure a hybrid cloud, Softchoice can help you chart the right course. Solutions such as Cloud Accelerator, as well as our experience in helping customers optimize their cloud governance and management strategies, provide a path toward a setup that works for you. Connect with our team today to learn more.

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