I'm looking to set up a virtual machine on Azure, but I've only worked with Windows Server versions 2022 and 2025 so far. I have an application that requires Windows Server 2016 as the latest compatible version. Is it possible to deploy this version in Azure, and if so, how do I go about it?
5 Answers
Yes, you can definitely run Windows Server 2016 on Azure! Many users, including myself, have migrated older versions like Windows Server 2003 and 2008, and they've worked fine. So, migrating to 2016 shouldn’t be a problem at all. Just follow the usual VM setup steps in the Azure portal, and you'll be good to go!
I’ve dealt with an application running on Windows Server 2008 R2 for SharePoint 2013, and had to upgrade it to 2012 R2. If you’re upgrading legacy apps, make sure all your dependencies are compatible with 2016, just to be safe.
If you're unsure about steps to create the VM, check out this guide on Microsoft’s site: https://learn.microsoft.com/en-us/answers/questions/109218/how-to-create-purposefully-outdated-virtual-machin. It can help you set it up properly!
Before you dive in, consider that Windows Server 2016 will reach its end of support in 2026. Do you really need to stick with this version for so long? Just something to think about!
If you’re concerned about accessing old data, having this VM on Azure could be a solid approach for keeping those applications running without issues.

Thanks for your input! We need this version because our company requires access to historical data for a few more years.