4 Ways to Handle Windows Server 2008 End of Support

Migrate to the cloud | Binary Tree

As you’ve probably seen, Microsoft announced the end of support for Windows Server 2008  and 2008 R2 on January 14, 2020. On this date, security updates from Microsoft will stop (unless you extend them, as we will talk about below). Your servers will be at a greater risk of being hacked, and you might no longer meet your compliance requirements.

 So now is the time to plan your migration and upgrade strategies. Below, we cover several options for next steps, plus the pros and cons for each.


Option 1: Keep your servers as is

You certainly have the option to keep your on-premises servers running on Windows Server 2008. It’s not something we recommend long-term, but it can buy you time.

The good news is that Microsoft gives you the option to buy Extended Security Updates for three years for any on-premises servers running Windows Server 2008 and 2008 R2. To be eligible for this option, you need active Software Assurance or Subscription licenses under an Enterprise Agreement.

Our rank: LOW

Why: You’re delaying the inevitable and not taking advantage of the latest security, performance, and innovation

Option 2: Upgrade on-premises servers

Another option is to keep your servers on-premises and upgrade them to Windows Server 2016. This way, you’ll keep getting regular security updates and can take advantage of new features and performance. The downside of this option is that you miss the opportunity to innovate even more and get to the cloud. You’ll spend time and effort on an upgrade without getting to the true finish line.

Our rank: MEDIUM

Why: It’s a good start, but you miss the opportunity to take advantage of the cloud

Option 3: Re-host servers as is to the cloud

Another way to start taking advantage of new cloud features is to rehost your servers to Azure as is. You can migrate servers running Windows Server 2008 workloads to Azure and get three years of Extended Security Updates at no additional charge. Later, when you’re ready, you can then upgrade to a current Windows Server version.

You can also use your existing Windows Server 2008 licenses in Azure and save up to 80% on Azure Virtual Machines with Azure Hybrid Benefit and Reserved Instances.

Our rank: HIGH

Why: Complies, but delays the server upgrade for up to 3 years

Option 4: Migrate to the cloud + upgrade

This is the most ambitious option, but it can also be the most efficient transition, with fewer detours on the way. Here, you migrate your servers to the cloud and also upgrade them to the latest version. 

Our rank: BEST

Why: It’s an efficient way to stay compliant and secure, with maximum performance and innovation

Ready to get started? We can help.

Don’t let your infrastructure and applications go unprotected. We at Binary Tree can help you take advantage of this opportunity and migrate to current versions for greater security, performance, and innovation. Our Domino on Azure service can help you move your legacy on-premises servers to Microsoft Azure—and manage them once you get there, in your tenant or ours.

Contact us to discuss how we can help you today.


For more related information, read our past blog posts: