Time to upgrade: How to prepare for Windows Server 2008 end of support

Steve Luper, Cloud Solution Architect

Jeff Mitchell, Cloud Solution Architect

The end is nigh! End of support for Windows Server 2008 is right around the corner, coming on January 14, 2020.

I know what you’re thinking: “My customers’ Data Center Migration’s got time, that’s over a year away.” I would encourage you to dig deeper into that thought. Halloween has passed, and we’re now heading into the holiday season. Next thing you know, it will be 2019 and you’ll have less then a year remaining on the end of support timeline.

For our partners, the time to start is now! Customers can choose from one of three options:

  1. Upgrade to Windows Server 2016 or 2019 and continue running on-premises
  2. Migrate Windows Server 2008 into Azure to become eligible for 3 years of free Extended Security Updates
  3. Modernize applications that are running on your at-risk servers into containers (and ideally run them in Azure)

In-place upgrade

Be aware that there is no direct path to upgrade from Windows Server 2008 to Windows Server 2016 and beyond. First, you’ll need to upgrade to Windows Server 2012, and to Windows Server 2016 from there. Also know that you won’t be able to change from 32-bit to 64-bit in the upgrade process. No need to worry if reading about this process make you uncomfortable? Visit our Upgrade Center to learn more and get the help you need.


Azure Site Recovery recently announced support for migrating Windows Server 2008 into Azure including 32-bit versions. As mentioned above, customers who move their Windows Server 2008 workloads into Azure virtual machines will receive 3 more years of extended security updates free of charge.

If you and/or your customers already have a preferred migration tool, don’t feel like you have to choose Azure Site Recovery. Check with your tool vendor to see if they support moving Windows Server 2008 into Azure.

Another opportunity to explore is migrating those Server Roles. You can certainly migrate traditional server roles like Active Directory, File Servers, RDS, and IIS by deploying a new modern server instance, then promoting the new server to take over from the aging Windows Server 2008 Server Roles.


For the final option, evaluate the Application being hosted on Windows Server 2008 to run in Containers or run on one of Azure’s many PaaS Services, like Azure SQL Database and Web Apps.

You could even choose to deliver the app differently using Application virtualization with RDS, Citrix, or VMware.

In terms of total cost of ownership, Azure is the most cost-effective cloud destination for customers with Windows Server 2008 workloads. We’ve illustrated a cost model that shows how AWS can be up to 5 times more expensive than Azure.

We’ve gathered some of the resources partners have found most helpful:

For more technical information, check out the following:

Finally, please join us as Steve Luper, Jeff Mitchell, and Jeff Wagner host the Azure Apps and Infrastructure Community Call on November 16 at 9:00 am PT

Applications and Infrastructure Technical Community