Windows Server 2008 has reached end of life, which typically means upgrading to a newer version. But CIOs have options beyond updating to a more recent iteration of Windows server, including staying put or migrating to the cloud.

If you still have workloads running on Windows Server 2008, you’re not alone. As recently as July 2019, Microsoft executives at the company’s Inspire partner conference estimated that up to 60 percent of Windows servers were still running Windows Server or SQL Server 2008. Some users had been delaying upgrades because of technology changes introduced in Windows Server 2012 that broke application compatibility.

Businesses that have stuck with Windows Server 2008 won’t notice the absence of support until February’s Patch Tuesday, as Microsoft released a security update on the last day of support, Jan. 14. The company’s support web pages say it will provide no more patches for the OS, although that’s not strictly true.

Microsoft’s server products begin life with “Mainstream Support,” including security and feature updates. For Windows Server 2008, that ended in 2015, with mainstream support for Windows Server 2008 R2 ending the following year.

Since then, both versions of Windows Server 2008 have been receiving what Microsoft calls “Extended Support,” which includes only security updates. This gives businesses an extra three years or so to pick the right moment to update to a newer version of Windows Server.

Even now, with the end of Extended Support, Windows Server 2008 isn’t dead. Enterprises that want to hold onto the OS for a little longer can sign up for Microsoft’s Extended Security Update Program and receive fixes for another three years — for an annual fee of around 75 percent of the license price.

Microsoft describes this option of doing nothing but cutting a check as a “last resort.” After that, it really is the end.

There is another way to obtain extended security updates, and that is to move on-premises Windows Server 2008 workloads to Microsoft’s Azure cloud, running them as-is on a VM or managed instance. For enterprises that pay for its hosting service, Microsoft says it will throw in three years of security updates for free.

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