End of Support for SQL Server and Windows Server 2008: Should You Migrate to the Cloud?

Written by Joe Kozlowicz on Thursday, June 6th 2019 — Categories: Active Directory, Cloud Hosting, IT Modernization, Microsoft, Security

You would be woefully uninformed and unprepared as an IT admin if you didn’t know that two major Microsoft products, the 2008 versions of SQL Server and Windows Server, are each about to reach their end of support. That means it’s time to upgrade or migrate lest you fall victim to inevitable security vulnerabilities.

One big question when facing a major software upgrade such as this is whether to remain in place, so to speak, and update to the latest version from your current deployment scenario on premise or in a hosted environment, or to move to a cloud-based server – namely Azure, since that offers you tight integration and lower costs with Microsoft products such as these.

SQL Server end of support is imminent, coming up on July 9, 2019. Windows Server has a few months to go, ending support on January 14, 2020.

You have three main upgrade paths. The choice is yours.

Postponing the Inevitable

You can receive three more years of extended security updates from Microsoft with two options: purchasing it for your existing deployment or migrating your 2008 workloads to Azure. If you move to Azure in this lift-and-shift scenario without updating the SQL or Win Server version, you’ll get three more years of security updates for “free.”

Of course, there are costs involved in a cloud migration if you aren’t already hosted in Azure. And if you’re doing the groundwork to migrate to the cloud, you’re probably better off starting with Azure-hosted PaaS versions of Windows Server or SQL, and spending your heavy lifting on refactoring your apps to use the latest versions.

Upgrade in Place

Licensing the latest versions of each platform – Windows Server 2016 and SQL Server 2017 – buys you at least six years of guaranteed support (and seven for SQL) as Microsoft offers a decade of support for all major releases.

You’ll have to upgrade to Windows Server 2012 before you can upgrade to 2016. Ideally this keeps all of your server roles and settings intact. If you have specific hardware drivers from your OEM they could cause problems. You can’t move from 32-bit to 64-bit architectures or from one build type to another, nor can you change the language. Your hardware will also need to meet the requirements for 2012 and 2016.

With SQL Server you can upgrade directly to 2017. You’ll need to enable Windows Authentication for SQL Server Agent and verify its default configuration. You also need to confirm you meet server and OS requirements. If you’re running SQL Server in a 32-bit instance, you can not upgrade directly to 2017 as it is 64-bit. You’ll instead need to backup or detach your databases and then reattach them to a new 2017 server, as well as re-creating your account credentials and user objects.

Windows Server 2019 is also in public preview, so you could take this chance to get a jump start and move all the way to the very latest and greatest.

Migrate to a New Server

Even if you remain on premise or in a hosted environment that is not Azure, you may want to provision a new physical or virtual server to host the new version of your Microsoft server product. Microsoft recommends this for Win Server 2016.

In this case you’ll set up your new Windows Server and move each individual role or feature from your previous server to the new one. You’ll still need to migrate to 2012 before 2016 and there will likely be downtime involved.

Migrate to Azure Cloud

If you’re likely to face a migration scenario regardless, moving to Azure-based PaaS or IaaS for your Windows Server and SQL Server deployments can offer some additional benefits.

Of course, there are the usual cloud suspects of shifting from capex to opex if you would have needed to purchase new physical servers. But you also add innovation, take a step on your digital transformation journey, and increase your security posture.

Even if migrating to Azure VMs and keeping your 2008 license might be delaying the inevitable, it does give you three more years to remain secure while planning your upgrade. You won’t need to make very many application code changes or adjustments and you can use your existing license.

You can also go ahead and switch to an Azure SQL Database Managed Instance for your SQL Server workloads; or perform the Migration scenario detailed above with an Azure Windows Server Virtual Machine running Windows Server 2016 as your destination.

If you’ve been putting off a cloud migration this end of support situation is an ideal opportunity to begin moving production servers into Azure. Be sure to read up on Migration Guides.

First of course. You’ll gain added functionality and features like Azure App Services, Azure IaaS, security tools like Sentinel, and additional data platform products like Power BI and Analytics Platform System. All of these cloud hosted services work together to help you foster business innovation and transformation rather than supporting your base infrastructure.

Why You Might Want to Stay In Place

Adding three years of security and stability might be appealing however. Windows Server is the base for a wide variety of enterprise applications and data, so downtime for updates and troubleshooting is not ideal. You’ll have to take a comprehensive application and data storage inventory before upgrading or migrating; and services like Active Directory are also likely to be disrupted or considered for cloud migration, especially if you host them on premise for SSO.

You may also have a legacy application that will only work on your old version of SQL or Windows Server. It’s up to you to weigh the risk and expense of migrating that app functionality to a new application or SaaS vs. maintaining security and compliance by updating.

Like any other cloud migration, you might also face concerns about data sovereignty or compliance. Although cloud providers including Azure now offer a wide range of compliance assurances, for some shops apps and data with high security simply must remain on premise.


Ultimately the decision is yours, but you have to make it really quite soon. Green House Data can help you map out the upgrade path that makes the most sense for your business with minimal disruptions to users or mission critical apps. We can also help you navigate licensing through the CSP program.

Our opinion may be slightly biased, but an end of support situation like this offers a fantastic opportunity to modernize your IT and start moving workloads into the cloud. You should take advantage and at least experiment – virtual servers can always be migrated to a private cloud or back on premise.