Windows and SQL Server 2008 and 2008 R2 End of Life Have Arrived: Now What?

Sreeraj Vasukuttan

I often imagine Windows Server 2008/2008 R2 and SQL Server 2008/2008 R2 as mighty old dinosaurs that lived for millions of years, waiting for that giant asteroid to fall from the sky. It’s a sad beginning, but read on and I’ll point you towards a few transformational paths that could save them both on the land and in the cloud.


Extended Support Dates in Effect

Windows Server 2008/2008 R2 and SQL Server 2008/2008 R2 have both met their end-of-life dates: July 9, 2019 for SQL Server 2008/2008 R2 and January 14, 2020 for Windows Server 2008/2008. If you’re still running any of those machines, you’re doing so at your own risk—especially in this age of cyberattacks.

The good news is that the fate of these dinosaurs is not quite as bad as the real ones that lived millions of years ago. It’s not that you can deflect the end-of-life asteroid by sending a space rocket at them; it’s that our mighty old dinosaurs can take a few evolutionary paths to exist in the Microsoft universe (in their current form or even fancier new forms).

Wandering Down Three Microsoft Paths

Path 1: The first path is the traditional evolutionary path of upgrading to a newer version of Windows Server and SQL Server. Here, you get the most updated features and a sought-after security landscape. The latest versions of Windows Server and SQL Server available are Windows Server 2019 (reaching general availability in early October 2018) and SQL Server 2017. You can upgrade to the on-premises versions or the cloud version on Azure (recommended by Microsoft). I would also like to mention Windows Server 2019 if you are thinking of going for the latest version. The only caveat for upgrading to the latest version of the on-premises server product is the price change. Check out this blog post to get a clearer picture of how price changes might affect your organization.

Path 2: If you do not want to upgrade to the latest server versions—don’t worry—Microsoft has you covered. Microsoft announced a few options for those who want to continue on Windows Server 2008/2008 R2 and SQL 2008/2008 R2. Through free Extended Security Updates (ESU) in Azure you can continue to host your Windows Server/SQL Server 2008/2008 R2 instances for three more years. That means you can continue running them in Azure until January 14, 2023 (Windows Server 2008/2008 R2 ) and July 12, 2022 for SQL Server 2008/2008 R2). On July 14, 2021, Microsoft announced that they are extending the free ESUs one more year. This means you could continue running SQL Server 2008 and 2008 R2 free in Azure until July 12, 2023 and Windows Server 2008 and 2008 R2 for free in Azure until January 14, 2024.

To save more money, you could simply move your Windows Server 2008/2008 R2 and SQL 2008/2008 R2 to Azure by using the Azure Hybrid Use Benefit. The only cost you would incur would be compute and infrastructure. With the use of Azure Reserved VM Instances for Windows Server and Azure SQL Database Reserved Capacity, you can also save further on the compute cost.

Path 3: The last path is to not evolve at all. Microsoft also announced extended security updates. You will be allowed to run Windows Server 2008/2008 R2 and SQL 2008/2008 R2 for 75% of the current operating system cost, and continue to receive security updates. For this extended support, you must have Software Assurance or the Enterprise Subscription agreement. This extension option is also a direct replacement for Windows Server and SQL Server Premium Assurance, that Microsoft discontinued prior to the announcement of this new option. Windows Server 2008/2008 R2 and SQL 2008/2008 R2 were the ones set to take advantage of the Premium Assurance offer. Customers only receive three years of these extended security updates, instead of the six years they would have received with the old Premium Assurance. However, on the FAQ part of the extended support announcement, Microsoft says they will honor the commitment for those who have already bought the Premium Assurance.

Sreeraj Vasukuttan is a Technical Marketing Manager at Connection with a passion for technology and marketing. He enjoys writing about cloud, security, and end-user compute. In his free time, he loves watching films, cooking, and traveling with his family.