Windows Server 2008 has reached end of life, which usually means upgrading to a newer version. But CIOs have options beyond updating to a newer 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% of Windows servers were still running Windows Server or SQL Server 2008. Some users had delayed updates. upgraded due to technology changes introduced in Windows Server 2012 that broke application compatibility.
Businesses that stuck with Windows Server 2008 won’t notice the lack of support until February Patch Tuesday, as Microsoft released a security update on the last day of support, January 14. The company’s support web pages say it will no longer provide patches. for the operating system, although this is not strictly true.
Microsoft’s server products begin life with “Mainstream Support,” including security and feature updates. For Windows Server 2008, this ended in 2015, with mainstream support for Windows Server 2008 R2 ending the following year.
Since then, both versions of Windows Server 2008 receive what Microsoft calls “extended support,” which only includes security updates. This gives businesses about three more years to choose the right time to update to a newer version of Windows Server.
Embrace and prolong
Even now, with the end of extended support, Windows Server 2008 is not dead. Businesses that want to keep the operating system a little longer can sign up for Microsoft’s Extended Security Update program and receive fixes for an additional three years for an annual fee of approximately 75% of the price of License.
Microsoft describes this option to do nothing but cut a check as a “last resort.” Then it’s really the end.
Another way to get Extended Security Updates is to move on-premises Windows Server 2008 workloads to Microsoft’s Azure cloud, running them as-is on a virtual machine or managed instance. For businesses that pay for its hosting service, Microsoft says it will offer three years of security updates for free.
Migration to the cloud
Amazon Web Services has another idea: migrate workloads to its cloud instead of Azure and upgrade to a newer version of Windows at the same time. Its End-of-Support (EMP) Migration Program for Windows Server offers a way to decouple applications from the underlying operating system, wrapping them in a compatibility layer that redirects calls to APIs that have changed. The software to do this is free, but AWS or its partners will charge a fee to assess and repackage the applications – and, of course, to host them in the AWS cloud.
Organizations moving on-premises workloads to clouds other than Azure will need to carefully review their documents. Last October, Microsoft changed its rules, requiring customers transferring on-premises Windows licenses to certain vendor clouds to pay additional fees for Software Assurance and mobility rights.
Against these cloud and licensing costs, CIOs will have to weigh the benefits of moving away from the old, unreliable hardware their applications were running on.
The upgrade path
Finally, there’s the conventional route to consider: upgrading from Windows Server 2008 to a version that’s still supported.
This is a multi-step process, the first of which is to upgrade to Windows Server 2012. General support for this has already ended and extended support will only work until 2023 .
From there, it’s another jump to Windows Server 2016, which has general support until the end of 2022, and then a final jump to Windows Server 2019 for full support until 2024.
Organizations running the R2 version of Windows Server 2008 can skip a step and upgrade directly from 2012 R2 to Windows Server 2019.
Microsoft’s documentation on this process explains why so many companies have decided to stick with the older operating system, noting that not all server roles and applications are supported in newer versions. and warning that careful planning of the update process is necessary to avoid surprises.
That’s sound advice, whether it’s updating, migrating, expanding, or doing nothing: only a careful assessment of a company’s situation can point the right way forward.
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