Windows Server 2008 and Windows Server 2008R2 are approaching the end of their support life cycle. After 14-Jan-2020, there will be no additional free security updates on-premises, non-security updates, free support options, or online technical content updates.
There are only three ways to get support moving forward for Windows Server 2008/2008 R2 licenses. First, you can purchase extended support for three years, which is the most expensive route. This can only be accomplished directly with Microsoft and you would need to be in an Enterprise Agreement directly with Microsoft.
Second, you can convert your current OS to a newer OS that is supported, and this can be accomplished through our Volume Licensing Team. The major issue here is around any applications you have being compatible with a newer OS.
Finally, you can move that workload to Azure, which will allow you three (3) years of free support while testing applications on newer operating systems to beat the 3-year end-of-life deadline.
You can migrate your on-premises Windows Server 2008 and Windows Server 2008 R2 servers to Azure, where you can continue to run them on virtual machines. In Azure you'll stay compliant, become more secure, and add cloud innovation to your work. The benefits of migrating to Azure include:
Our Cloud & Automation Team can help with the Migration Services.
We recommend that you migrate to Azure or upgrade to the current product versions before the support end dates. This lets you take advantage of the latest product innovations and make sure you have uninterrupted support from Microsoft.