Windows Server and SQL Server 2008/2008 R2 End of Life Is Fast Approaching—Are You Ready?


SQL Server 2008 end of life is on July 9, 2019, and Windows Server 2008 end of life is on January 14, 2020. The clock is ticking, and you could be at risk if you don’t migrate to Azure or update your current on-premises software now.

The ends of life of SQL Server 2008/2008 R2 and Windows Server 2008/2008 R2 are the two big upcoming events on the Microsoft end of life calendar. Connection has been working with a lot of our customers to prepare them for the transition. Check out our initial blog post on the same topic. If you are still scratching your head, trying to figure out what is your best option, don’t worry—we’re here to help. Connection, as your Microsoft partner, is fully equipped to provide the right guidance and assistance to help you with this transition.

You have a few options to move forward. The first option is to upgrade on-premises servers and to plan for a future hybrid environment. For applications that must remain on-premises, you’ll want to upgrade to cloud-ready Windows Server 2016 or 2019 and SQL Server 2017 or 2019 for the most current security, performance, and innovation features. Take advantage of built-in hybrid cloud capabilities for backup and high availability or migrate later.

The second option is to migrate these workloads to Azure. End of support is a good time to evaluate new options to innovate and modernize with cloud technologies. Take the first step by migrating 2008 applications and data to Azure, where you can get free Extended Security Updates for three more years. There are three reasons I would recommend migrating a 2008 server application to Azure. They are innovation, cost savings, and security and compliance.


By migrating, you have the opportunity to embrace the tools in Azure to modernize these business applications. Fully managed services such as Azure SQL Database, Azure App Service, and Azure IaaS will free up your IT team from day-to-day maintenance and allow them to focus on innovating to advance the business.

Cost Savings

With Extended Security on Azure, you will get three years of extended security updates at no additional charge and can upgrade to a current version when ready. You can re-host your 2008 Server workloads in Azure and reduce infrastructure cost. Using existing licenses, you can save up to 80% on Azure virtual machines with Azure Hybrid Benefit and Reserved Instances.

Security and Compliance

Thousands of critical business applications around the world run on SQL Server and Windows Server 2008 and 2008 R2. Those versions will face security and compliance risks when support ends. Organizations that run these applications without making regular security updates will be more vulnerable to cyber attacks which could expose user and business data. Taking steps now to safeguard your environment will help prevent these possible data breaches—and also keep you from incurring legal penalties. Microsoft Trust Center has a full list of compliance offerings for our public sector and government customers to review. Some of the highlighted compliance offerings include FIPS 140-2, ITAR, and NIST Cyber Security Framework, also known as CSF.

With Microsoft’s cloud-powered, intelligent security solutions, you can protect users, data, and everything in between. Prevent identity attacks with Azure AD Identity protection, Azure ATP, and Microsoft Cloud App security. Protect data, apps, and infrastructure quickly with built-in security services in Azure that include unparalleled security intelligence to help identify rapidly evolving threats early, so you can respond quickly. Implement a layered, in-depth strategy across identity, data, hosts, and networks. Unify security management and enable advanced threat protection across hybrid cloud environments.

The Last Resort

If you cannot upgrade your servers or take advantage of the free Azure Extended Security before the deadline, the last option you have is to go for paid Extended Security Updates from Microsoft to keep server workloads protected. Buy Extended Security Updates annually for up to three more years. Cover only the servers you need. This is a costlier option that you might want to consider if you need to keep things as they are for the next three years.

How Connection Can Help

If you need more support to make the right choice, engage with our LSS team. Our Microsoft LSS teams work with our customers daily on these specific migrations.If you want to achieve greater clarity and control of your software environment, optimize your Microsoft licensing, and keep your investments strong over time, you need a partner with the right expertise. Connection has built an expert Microsoft licensing team over the last decade and developed unique licensing skill sets proprietary to us, including our Microsoft Licensing Optimization (MLO) process. MLO is a progression of licensing analyses, unmatched in the Licensing Solution Partner (LSP) community. Our MLO analyses provide you comprehensive, cost-efficient, business-driven strategies, while enabling you to realize greater control over your licensing agreements.