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Windows Server 2008 End of Life is Coming: Now What?

Cloud | Posted on April 3, 2019

The Windows Server 2008 end of life date is almost upon us.

On Jan. 14, 2020, Microsoft will no longer offer extended support for Windows Server 2008 and 2008 R2, meaning these platforms won’t receive any additional security patches or other updates. Their workloads will need to be migrated to newer environments – whether that entails rehosting them in Microsoft Azure cloud or keeping them on-prem by upgrading to Windows Server 2012 and later.

As this date approaches, it’s time to ask yourself an important question: What’s the best way to transition away from a Windows Server 2008 or 2008 R2 deployment? Let’s first take a look at the general stakes for making the upgrade and then explore the specific options for seeing it through.

Risks of running Windows Server 2008 beyond support lifecycle

To understand the pitfalls of continuing on with either version of Windows Server 2008, we can look back on what happened to Windows Server 2003 in 2015. On the eve of its end-of-support date that year, Server 2003 was about to become vulnerable to many new threats like malware and web attacks, in addition to violating regulations such as HIPAA in the U.S. 

A similar set of risks now looms over Windows Server 2008. Sticking with it will:


  • Drive up support and maintenance costs. Propping up Windows Server 2008 past January 2020 will incur significant overhead, in the form of customized security, relatively poor performance, and possible incompatibilities for some line-of-business applications. Compliance violations and failed audits could further increase these costs.


  • Impede access to the latest functionality. Newer versions of Windows Server not only have stronger security, they also contain more features. Plus, remaining in a Server 2008 environment comes with the opportunity cost of missing out on the potential benefits of a Microsoft Azure migration.


Overhauling something as central as a Windows Server implementation can seem daunting, as shown in our 2015 survey that found 21 percent of servers were still running Server 2003 mere months before its support ended. The good news is that there are multiple viable options for making the switch.


Options for Windows Server 2008 End of Life

Upgrading from Windows Server 2008 and 2008 R2

One of the first questions to answer when considering an upgrade from Server 2008 or 2008 R2 is whether the environment will remain on-prem/hosted, or be shifted to the cloud. 

For the former route, there is the option to purchase Extended Security Updates from Microsoft or a licensing partner from March 1, 2019 on. Microsoft has also charted an overall path for on-prem upgrades of Server 2008 and 2008 R2, which involve updating to Server 2012 first and then to Server 2016 and Server 2019. Windows Server 2019 offers multi-layered security, hybrid capabilities with Azure, and other features for modernizing apps via technologies like containers.

Windows Server 2008 End of Life Upgrade Paths

Azure itself provides an alternative upgrade route in the cloud. Existing Server images can be migrated for free and three years of Extended Security Updates are included at no additional cost. Rehosting a Windows Server environment in Azure provides access to features such as its managed database, app service, and IaaS resources. The Azure approach will usually be more cost-effective than keeping Windows Server on-premises or hosting it in another cloud like AWS. 

No matter which upgrade option makes the most sense for your organization, we are here to help guide the process. Connect with our team to learn more about solutions such as Cloud Accelerator that can make your upgrade easier.

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