Skip to content
Windows Server Blog

Over the last couple of years, we have shared why it is business critical to migrate and upgrade apps and services running on Windows Server 2008 and 2008 R2. As you are aware, on January 14th, 2020, support for Windows Server 2008 and 2008 R2 will end. To ensure that your apps, service, and data are protected, we recommend migrating to supported OS versions such as Windows Server 2019. 

Now, if you’re reading this today, you probably still have some workloads that won’t upgrade before the deadline. The good news is that we have options to keep you protected and putting you on a path to modernize your infrastructure and apps.

Let’s look at these options.

Extended Security Updates keys are available from Azure portal

For apps and services that need to run on-premises on Windows Server 2008 and 2008 R2, Extended Security Updates can be purchased under eligible programs. Please visit our site for the most up to date information including our frequently asked questions.

We recently published this Tech Community blog on the steps to purchase, install, and activate Windows Server 2008 and 2008 R2 extended security updates keys. If you’re unsure whether your servers are ready to receive extended security updates and like to test, refer to KB4528069 for Windows Server 2008 R2 SP1, and KB4528081 for Windows Server 2008 SP2.

Additionally today, we are sharing that you can now join a preview of extended security updates (in the Azure portal), which will allow you to obtain eligible unlock keys from the Azure portal. To get started, go to extended security updates for Windows Server in the Azure portal. Please visit tech docs for detailed documentation. 

Migrate to Azure and upgrade when you are ready

Azure offers one of the most effective ways that gives you more time to modernize. Windows Server 2008 and 2008 R2 Virtual Machines (VMs) on Azure get 3 years of free Extended Security Updates, giving you the opportunity to invest more time towards modernizing your app stack while staying secured.

With the Azure hybrid benefit you can save 40 percent off the total cost of a virtual machine. Combining the Azure Hybrid Benefit with Azure Reserved Virtual Machine Instances, you can realize up to 80 percent savings on the total cost of a VM. Azure hybrid benefit works for both Azure Virtual Machines and Azure Dedicated Host.

To get started and assess your app dependencies such as on domain controllers use Azure Migrate. It is a free and agentless tool to discover on-premises servers, assess dependencies, and migrate apps to Azure.

It’s critical to choose the right path for the right Server Role. We’ve laid out the options for you here, and for more detailed reading, check out the Windows Server migration guide.

A diagram showing the recommended migration paths for Windows Server Roles

Secondly, evaluate your migration options based on your business requirements. Azure offers several lift and shift options. Windows Server 2008 and 2008 R2 apps can be migrated to any of the following options and then, upgrade to Windows Server 2019 or Windows Server 2016.

Now, most of our customers are running lift-and-shift Windows Server 2008/R2 migrations and app modernization efforts in parallel. Apps and services that lend themselves to quick modernization can take advantage of services such as App Service and Azure Kubernetes Service, which supports Windows Server containers. Please note Windows containers are available in versions Windows Server 2016 onwards. App Service works great for web apps written in .NET Framework and .NET Core as well as other frameworks such as Node.js, Java, PHP, Ruby, and Python. For modernizing with containers, Azure Kubernetes Service can help to easily deploy and manage those apps.

And finally, to help you with this transition to the cloud, we launched the Azure Migration Program, which offers step-by-step guidance for migration. This program was created in collaboration with well-known and trusted partners and service providers, each of whom has a deep understanding of Windows Server.

Now, let’s look at the scenario where you need to run Windows Server apps and services on-premises.

Upgrade on-premises

Over the past year, we launched the most innovative version of Windows Server yet, with Windows Server 2019. For workloads that you know will stay on-premises Windows Server 2019 offers the latest advances in security such as Advanced Thread Protection to detect attacks and zero-day exploits and Defender Exploit Guard to help combat ransomware attacks. Windows Server 2019 with several built-in hybrid features such as Storage Migration Service and Azure Network Adapter. This ensures that your apps, services, and data are all secured and ready for a move to Azure whenever you’re ready.

For modern apps, Windows Server 2019 offers improved app compatibility for containers and support for Kubernetes. Learn more about Windows container in our documentation.

On-premises, you can also take advantage of Windows Admin Center, a modern server management tool to manage Windows Server environments. Windows Admin Center offers connections to Azure services for Backup, and Disaster Recovery. Check out the Windows Admin Center tech docs to get started today.

And finally, for those of you using Azure already, the newly announced Azure Arc can centrally manage servers on Azure and on-premises.

More resources

Here are some learning path presentations to help you get started:

Finally, join us in the Windows Server Tech Community to keep up to date with experts around the world, and stay tuned for the next Windows Server Summit to learn more about the latest innovations. We’re looking forward to hearing from you.