With the End of Support for Windows Server 2008 on January 14th, 2020 - you no longer have the ability to receive Security Updates or Support for any servers running Windows Server 2008. If you need to keep these systems under some level of support after January 14th - you have a few limited options:
- You can migrate your Server and workload up to Azure and receive up to 3 free years of Security Updates and Support from Microsoft.
- Provided you have an Enterprise Agreement / Volume License Agreement or you have purchased Software Assurance - you can enter into an Extended Support Agreement with Microsoft for up to 3 years and you will be able to register / enroll a fixed number of systems into this program.
If you NEED to stay on-premises with these systems, and you have all the prerequisites in place, you can generate a special "Multiple Activation Key" from the Azure portal and deploy it to your on-prem update service: Windows Update, System Center Config Man or even 3rd party solution.
Want to learn more? I've got you covered. I asked Ned Pyle - Principal Program Manager on the Windows Server Team to talk about your options and show us how to generate MAK keys. For more details and documentation about this process - check out this article which has all the info.
Did we miss anything? Let us know in the comments and we'll do our best to get you the info you need!