If you’re running Windows Server or SQL Server 2008 or 2008 R2, these versions are reaching the end of their support lifecycle. Each version is backed by a minimum of 10 years of support (5 years for Mainstream Support and 5 years for Extended Support) including regular security updates. End of support means the end of security updates, which can cause security and compliance issues as well as put applications and business at risk. We recommend upgrading to current versions for the most advanced security, performance, and innovation. Keeping your Servers within mainstream support or at least Extended support is vital to business continuity.

For Windows Server 2008 and Windows Server 2008 R2, end-of-life mainstream support ended January 14, 2015—and Microsoft ends Extended Support on January 14, 2020.

Likewise, Extended Support for SQL Server 2008 and 2008 R2 ends July 9, 2019. The database is often tied to one or more applications running on Windows Server, so it makes sense to look at both as you build your EOS(End of Support) plan.

Many organizations are running workloads on Windows Server 2008 and 2008 R2. You can continue to use Windows Server 2008 R2 safely in your environment’s architecture, at least until the extended support expiration date, January 14, 2020.

If you put off action, however, you will stop receiving regular security updates, putting your server workloads at risk. We always recommend running current versions of software for the most advanced security, performance and features. Plus, you are always protected with regular security updates.Security issues

Security is a top priority for IT teams. New threats have made it harder than ever for IT to secure data and applications. Windows Server 2016 gives you new capabilities to help prevent attacks and detect suspicious activity, with features to control privileged access, help protect virtual machines, and harden the platform against emerging threats.

Organizations have options. You may use multiple options to move workloads from Windows Server 2008/2008 R2, depending on the workload.

  • Do you want to keep the workload on-premises or move to the cloud?
  • Can you upgrade the operating system?
  • Do you want rebuild the application using new app patterns with Azure PaaS – or simplify containerize to lift and shift with minimal code changes?

Microsoft has you covered across all options:

  • Move to Azure by choosing to Rehost, Refactor, or Rebuild your workload or app.
  • Or Upgrade on premises to the latest version of Windows Server.

In Azure:

If Azure is your destination, you can simply migrate apps running on 2008/2008 R2 as is – and get three more years of security updates for free. This buys you more time to work on upgrading or modernizing your applications in the cloud.

Many apps are tied to data, so we will also offer 3 years of free Extended Security Updates for SQL Server 2008/2008 R2 running in Azure VMs. Or, even better, migrate to Azure SQL Database Managed Instance for a version-free option that will make this your last end-of-support transition.


We recommend upgrading to the most current versions of Windows Server and SQL Server. If you cannot meet the deadline, you can buy Extended Security Updates to keep the remaining servers protected until you get them upgraded.

Windows Server 2016 was designed for today’s datacenters and helps you flourish under a new model that delivers faster time to value and innovation.

Many organizations, however, face strict compliance or business requirements. For organizations that need it all—security, efficiency, and innovation—Windows Server 2016 delivers it. Windows Server 2016 is the cloud-ready operating system that supports your current workloads while introducing new technologies that get you DevOps ready and make it easy to transition to cloud computing when you are ready.

Security: Windows Server 2016 includes built-in breach resistance to help thwart attacks on your systems and meet compliance goals. Even if someone finds a way into your environment, the layers of security built into Windows Server 2016 limit the damage they can cause and help detect suspicious activity

App innovation: Increasingly, organizations use apps to help differentiate themselves from the competition. Windows Server 2016 supports application innovation using container technology and microservices.

Software-defined efficiencies: As organizations push the boundaries of highly virtualized environments, they can use Windows Server 2016 capabilities to meet operational and security challenges, freeing up IT resources to plan a strategy that uses the cloud for future applications and solutions. Windows Server 2016 makes possible affordable, high-performance storage and Azure-inspired networking capabilities.

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