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The Big Carrot in Windows Server 2008-to-Azure Migrations

Microsoft is offering a big carrot to get organizations to Azure in combination with the stick of Windows Server 2008 end-of-support.

That stick that's feared across the IT landscape is that support is ending for Windows Server 2008 on Jan. 14, 2020. Specifically, Extended Support, which includes security updates, ends that day for Windows Server 2008 Service Pack 2, Windows Server 2008 R2 SP1, Hyper-V Server 2008 and Hyper-V Server 2008 R2 SP1.

It's a wide swath of the market that's still on those server operating systems. Microsoft recently estimated that 60 percent of its server installed base, or 24 million instances, remain on Windows Server 2008 and/or SQL Server 2008, which fell out of support last month.

The other part of the stick is that organizations that want to stay on Windows Server 2008 for some reason must enter into an expensive contract for Extended Security Updates (ESU) if they want any kind of security protection, and those are only available for three years.

The carrot is that Microsoft is offering another route for customers who don't want to, or are unable to, move off of Windows Server 2008 or SQL Server 2008 right away. The carrot is a sort of half-move.

What those customers can do is migrate their instances, as they are, to Azure. Customers who rehost Windows Server 2008 and 2008 R2 workloads directly to Azure will get three full years of ESU at no additional charge. That gives them the option of upgrading from Windows Server 2008 at a more leisurely pace within those virtual machines.

They'll be paying Azure hosting fees and be in the public cloud, but they don't have to pay the ESU, so their existing operations can continue largely as-is.

It's a serious move by Microsoft to make Azure very appealing to organizations that have been at the tail end of the cloud adoption curve.

While attractive, this is only one of the options for moving from Windows Server 2008 before the deadline. For more detail on options for on-premises, hybrid and cloud migrations, check out RCP's "Partner's Guide to the Windows Server 2008 Deadline" (registration required).

Posted by Scott Bekker on August 08, 2019


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