How to Manage End of Support for SQL Server 2008 and Windows Server 2008

Two major deadlines have been looming for agencies that use older versions of popular Microsoft products. SQL Server 2008 and SQL Server 2008 R2 reach their end of support on July 9. Windows Server 2008 and Windows Server 2008 R2 will hit their deadline six months later, on Jan. 14, 2020. 

With these deadlines, agencies using these products should already have made progress on their migration strategies. Fortunately, there are several options available to resolve the challenges involved, depending upon the circumstances facing each agency and each workload. Let’s take a look at the possibilities.

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Ignoring End of Life Is Not an Option

First, and most importantly, doing nothing is not a viable option. After the end of support, Microsoft will no longer provide standard support for these products. In addition to not supporting customers with issues, there is a more serious security impact: Microsoft will no longer release security updates for these products through the automatic updating process. That means that customers will be vulnerable to any new security issues identified after the EOS, with very few options for remediating the problem. That’s an unacceptable level of risk for almost any application.

Extensions Buy Time for SQL Server and Windows Server 2008 Users

The simplest option is to buy a way out of the problem. Push the deadline by up to three years by purchasing Extended Security Updates from Microsoft. This option is available only to customers using SQL Server or Windows Server with an active subscription to the Software Assurance licensing program. Customers purchasing Extended Security Updates may do so in one-year increments for up to three years before reaching the final deadline. 

It’s important to note that, while this addresses the immediate issue, it’s simply kicking the can down the road. When the final deadlines approach in 2022 and 2023, customers will need to migrate to a more current version of Windows and/or SQL Server.

Azure Virtual Machines Provide Some Help

Microsoft offers free Extended Security Updates to customers running Windows and SQL Server 2008 in the cloud using Azure Virtual Machines. This is essentially the same approach as purchasing extended updates for use on-premises but without the cost of the purchase.

This option isn’t the quickest approach because it involves the heavy lifting of moving workloads to the cloud. It also isn’t the most effective approach, because it also simply postpones the inevitable. However, it may be a reasonable option for agencies that are already planning to move to the cloud and face operational issues that prevent upgrades before the deadline. 

Upgrade to Windows Server 2016 and SQL Server 2017 

The most effective solution is to upgrade to more recent versions of these products: Windows Server 2016 and SQL Server 2017. Agencies should find that most of these upgrades won’t negatively impact functionality, but all production deployments should go through a standard testing and change management process. Upgrading installations resolves the immediate issue and avoids postponing the inevitable. Microsoft’s standard support policy is to offer software updates for 10 years following a product’s release, so agencies upgrading now won’t face another upgrade deadline until 2026.