Windows Server 2008 End of Support is Near. Here Are Your Upgrade Options.

Windows Server 2008 has enjoyed a 12-year run, but after multiple extensions, Microsoft will officially cut off support on January 14, 2020. Windows Server 2008 R2, which is just one year younger, will also reach end of support on that date. It should be quite the retirement party with the Windows 7 desktop operating system reaching its end of life as well.

Retirement is probably the wrong word, however, as these products will continue to function, and many organizations will continue to use them. As we’ve discussed previously, and as Microsoft and security experts have warned repeatedly, companies will be running unsupported products at their own risk.

Microsoft Support clearly states that end of support for Windows Server 2008 and 2008 R2 means there will be no more free security updates, non-security updates, support options or online technical content updates. In other words, vulnerabilities will go unpatched and technical issues will go unsupported.

Microsoft recommends that organizations running Windows Server 2008 and 2008 R2 migrate to the Azure cloud platform. The standard cloud value proposition applies to Azure – access to modern applications and services, ongoing upgrades to those tools, lower infrastructure costs, and robust security that can stop modern threats and satisfy compliance requirements. Azure also has the benefit of integrating seamlessly with on-premises Microsoft platforms to create a hybrid cloud environment. Every organization should conduct an assessment to determine whether a move the cloud is the best option.

If you need to have your server on-premises due to business requirements, contractual obligations or industry regulations, you should plan to upgrade to Windows Server 2016. However, you can’t make a direct leap from 2008 to 2016. You have to upgrade to Windows Server 2012 before you make the move to 2016.

While this step does add complexity to the migration process, you’re likely to find that the benefits of Server 2016 make it worthwhile. The development of Windows Server 2016 was largely driven by customer feedback, which focused on demand for improved security, a software-defined data center and a modern application platform.

From a security standpoint, Windows Server 2016 has multiple layers of protection built into the operating system to prevent attacks and enhance the security of your virtual machines and applications. With software-defined compute, storage and network virtualization, you’ll enjoy increased cost-efficiency, flexibility and management simplicity. Although Windows Server 2016 is an on-premises solution, it is a cloud-ready operating system that delivers the innovation promised by Azure and is optimized for traditional and cloud-native applications.

As you plan your migration strategy away from Windows Server 2008, make sure that you account for other Microsoft products that are nearing end of support. In addition to Windows 7, it’s the end of the road for SQL Server 2008 and 2008 R2 on July 9, 2019, SharePoint Server 2010 on October 13, 2020, Exchange Server 2010 on January 14, 2020, and Office 2010 on October 13, 2020.

With so many products reaching end of support, it can seem overwhelming to create a comprehensive migration strategy. Let us help you determine the best migration path for each product and develop a plan that minimizes risk and business disruption.