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3 min read

Maximize your Windows Server investments with new benefits and more flexibility

Customers like you, with businesses of all sizes, have trusted Windows Server as the platform to run your mission-critical workloads for over 30 years. Through challenging economic conditions and constantly shifting business needs, you’ve been able to adapt and innovate with support from a resilient infrastructure. We are committed to supporting you in the next steps to modernize by introducing new benefits that add more value and flexibility to maximize your Windows Server investments while achieving cost savings and efficiency.

Azure Hybrid Benefit expansion

As customers are increasing cloud adoption to run virtual machine (VM)–based and containerized applications, they also need to keep some workloads on-premises. At Microsoft, we are committed to meeting customers where they are. Azure Hybrid Benefit is a program that enables customers to reduce the costs of running workloads in the cloud. At Microsoft Ignite, we’re introducing new additions to Azure Hybrid Benefit to bring the value of Azure to where customers are.

As part of our updates, customers with Windows Server Software Assurance or a Cloud Solution Provider subscription will be able to use Azure Kubernetes Service (AKS) on Windows Server and Azure Stack HCI in their own datacenters or edge infrastructure at no additional cost. This will enable customers to containerize their applications and deploy them on Azure or on-premises consistently by maximizing business value with a managed Kubernetes service in their own environments.

For customers looking to modernize their environment, we are also introducing a new benefit for Windows Server Datacenter Software Assurance customers to use Azure Stack HCI at no additional cost.1 With this, customers can modernize their existing datacenter and edge infrastructure to run their VM and container-based workloads on modern infrastructure with industry-leading price performance and built-in connectivity to Azure. Learn more about Azure Hybrid Benefit for AKS and Azure Stack HCI.

More flexibility to run Windows Server

On October 1, 2022, we implemented several updates to outsourcing and hosting terms for customers and partners globally. Among these is the Flexible Virtualization Benefit, which allows customers with Software Assurance or subscription licenses to run their own licensed software, including Windows Server, on other cloud providers’ infrastructure—dedicated or multitenant.2 Additionally, customers can also license Windows Server on a VM basis.

Windows Server customers have been increasingly leveraging Windows containers to modernize their applications. However, we heard from a few of our customers and application vendors that needed the ability to distribute a complete containerized application directly to their end users. Starting today, customers will be able to redistribute Windows Container base images beyond their organization in accordance with the updated End-User Agreement License. Now, customers and application vendors across segments like medical, financial, manufacturing, or other air-gapped environments can more easily use Windows containers to modernize their applications. Learn more about the upcoming changes in our tech community blog.

Modernize for end of support

With all the added benefits and flexibility mentioned above, there is no better time to modernize than now. This is especially true if you are running Windows Server 2012/R2, which is reaching end of support next year on October 10, 2023. We have several options to keep your Windows Server 2012/R2 workloads protected:

  • Migrate to Azure and run securely with up to three years of free Extended Security Updates. This includes all Azure destinations such as Azure Virtual Machines, Azure Dedicated Host, Azure VMware Solution, and the Azure Stack portfolio.
  • Upgrade to Windows Server 2022 to get the latest innovation in security and application modernization.
  • Deploy extended security updates on-premises. Customers that cannot meet the end of support deadline and have Software Assurance or subscription licenses under an enterprise agreement enrollment, and cannot migrate their Windows Server to Azure, will have the option to buy Extended Security Updates.

Start migrating and modernizing your Windows Server workloads

No matter where you are in your migration and modernization journey, we are committed to supporting you at every step. Here are some resources to get started today:  


1Currently only available for Windows Server Datacenter licenses with Software Assurance purchased through Enterprise Agreements. Customers can only use Windows Server or Azure Stack HCI. Customers will have 180 days of concurrent use rights to move to Azure Stack HCI.

2Note that these changes exclude what we term Listed Providers: Alibaba, Amazon Web Services, Google, and Microsoft. Customers that want to use a Listed Provider for outsourcing can acquire licenses directly from the Listed Provider.

3Note: In alignment with the servicing model for Windows 7 and Windows 8.1 (link to blog), the Windows Server 2012 and 2012 R2 ESU program will only include Monthly Rollup packages; Security Only update packages will not be provided.