It's time to get off Windows and SQL Server 2012 (or run them on Azure)

The only way to get extended support for 2008 versions of Windows and SQL Server is in the cloud. Here's why you should be thinking about 2012 migrations now as well.

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Image: Shutterstock/Khakimullin Aleksandr

The release of Windows Server 2022 is a good reminder that older versions of the OS will be losing support and security updates soon, along with older versions of SQL Server. But if you're prepared to move workloads to the cloud, you get a little more flexibility.

SQL Server remains a significant workload for Windows Server; the 2022 release can support up to 48TB of RAM and 2,048 logical processors per physical server, specifically for SQL Server. So if you're still running Windows Server 2008 or 2008 R2, it's probably for a SQL Server 2008 workload. Not only are all three of those long out of extended support but they're about to stop getting Extended Security Updates too.

SQL Server 2008 and 2008 R2 stop getting ESUs on July 12, 2022, with Windows Server 2008 and R2 security updates ending on January 14, 2023, so you need to be planning now for how you will deal with upgrading or migrating those workloads.

If you're still running SQL Server 2012 and Windows Server 2012 or 2012 R2, you have a little more time to plan ahead for upgrading. Extended support for SQL Server 2012 (including the R2 version) will also end soon, on July 12, 2022; Windows Server 2012 and 2012 R2 extended support goes away on October 10, 2023.

At that point, you can pay for Extended Security Updates, which include critical and important patches, critical updates for SQL Server and access to support if you have an active support plan with Microsoft. They're distributed through the usual update channels, like Windows Update and WSUS.

SEE: Checklist: Server inventory (TechRepublic Premium)

ESUs for SQL Server 2012 and 2012 R2 will be available to purchase from April 2022 (so you know you won't miss any security updates when extended support stops). ESUs for Windows Server 2012 and R2 can be bought from July 2023.

ESUs are an expensive way of sticking with the older versions after the end of extended support. You have to have at least one month of Software Assurance or an Enterprise Agreement with subscription licences, you buy ESUs in in 2-core packs for SQL Server and 16-core packs for Windows Server 2012 and you'll be paying 75% of the licence cost for the latest version of SQL Server and Windows Server (not the version you're still running), just for the first year. For the second year, you're paying the same as the licence cost for the current versions and 125% of that licence cost for the third year.

The pricing escalator there is to discourage organizations from clinging to older versions, because each year you only pay for the servers you need; so the sooner you upgrade, the fewer servers you have to pay for at the next tier each year. You can't keep the price down by delaying: You can start using the ESUs in year two or year three—but you'll have to pay for the previous years even though you weren't taking the updates.

SEE: Windows Server 2022: A cheat sheet (TechRepublic)

You can buy ESUs for the Enterprise and Standard Editions of SQL Server 2012 and R2; you can't buy them for Express or Developer editions but if you're already paying for ESUs you can apply them to those editions (and they'll get ESUs if you run them in Azure). If you have a passive secondary server for failover from a production SQL Server workload (like a VM that's ready to go but not running), you can buy ESUs just for the production workload but also use them to keep the secondary up to date in the VM. If you have development or test servers licensed under Visual Studio or MSDN subscriptions, you can apply the ESUs you buy to those without needing to pay extra.

Whatever edition you're running, make sure you have the latest service pack applied or you won't be able to install the ESUs. You will have to use online servicing (or audit mode) to apply ESUs; you can't do it with DISM and offline servicing. And you'll be stuck on older versions of System Center. There are only a few scenarios that can be managed with System Center 2016 on these older workloads, although the latest release of Configuration Manager can deploy ESUs to them.

Ready to upgrade

Organizations on such old versions aren't likely to jump all the way to the brand new version of Windows Server. But they should be considering at least Windows Server 2019, which supports SQL Server 2016 and 2017 and gives you new options like running SQL Server in containers (although only the Linux version, as the Windows Container support for SQL Server never made it out of beta. There's a list of everything that's new since Windows Server 2012 here.

You also have the option of running SQL Server as an evergreen database service on Arc, on your choice of infrastructure, managed from Azure; that way you can avoid future big bang upgrades entirely.

Windows Server 2016, 2019 and 2022 support in-place upgrades from Windows Server 2012 or later, as long as you're running a 64-bit version (because there are no 32-bit version of Windows Server 2016 and later). So if you're on Windows Server 2008, you'll have to upgrade to Windows Server 2012 first and then to your target version of Windows Server; from 2008 R2 you can upgrade to 2012 R2 and then your final version.

For roles other than running SQL Server, it's worth checking the matrix of which server roles can be upgraded from Server 2012 and which will need to be migrated to new hardware running the new OS. For instance, Microsoft recommends that all domain controllers should be running at least Windows Server 2016 and in-place upgrades are not recommended; instead you need to set up a new server and promote that to domain controller.

SEE: A new Microsoft Store: What does it mean for you and your business? A lot, actually (TechRepublic)

Azure first, upgrade later

If there's a compelling reason not to upgrade your Windows Server and SQL Server workloads to something newer, the cheapest way to get extended support is to run them in a virtual machine on Azure, where you get free ESUs for three years after extended support ends.

If you move your 2008 or 2008 R2 workloads to Azure, you can get an extra year of free ESUs, taking you to July 12, 2023, for SQL Server 2008 and R2, and to January 14, 2024, for Windows Server 2008 and R2.

For SQL Server and Windows Server 2012 or 2012 R2, you'll get free ESUs on Azure until July 12, 2025; Windows Server 2012 and 2012 R2 extended support goes away on October 10, 2026.

If you move any of these SQL Server and Windows Server workloads to Azure VMs, ESUs will be enabled automatically so you don't have to do any configuration. But if you want automated patching for SQL Server, you need to register the VMs with the SQL Server IaaS Agent extension.

Migrating to Azure also lets you take advantage of other services, like Automanage. You can run standard Azure VMs or use the dedicated host, VMware or Nutanix options if that's what you're migrating from.

But moving your workloads to Azure doesn't mean you have to move them into the public cloud: You get the same free ESU deal if you run Windows Server and SQL Server on Azure Stack, whether that's Azure Stack Hub, Azure Stack Edge or Azure Stack HCI, all of which can run on your own hardware and on your own network. You do have to do a little extra work downloading SQL Server ESUs from the Azure portal but you don't have to pay for those continuing security updates, and you get the extra year of coverage for the 2008 and 2008 R2 products.

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