I have recorded a how to perform an in-place upgrade a Windows Server to Windows Server 2025 guide. I also created a visual diagram with all the supported paths. Hopefully this will be useful for businesses that want to apply an in-place upgrade to their Windows Servers. Microsoft recently announced the Windows 2025. With the introduction of the new product, they have also announced something that was not possible before regarding upgrade paths.
About Windows Server 2025 upgrade:
In the past, almost all Windows Server versions supported an in-place upgrade (also known as Feature update) only for the two previous versions. For example, you could update from Windows 2012 R2 and Windows Server 2016 to Windows Server 2019, etc.
Windows Server 2025 is the first ever Windows Server OS that supports featured upgrades from the 4 previous versions! This shows Microsoft’s commitment to giving help to all businesses to get to the latest version easily even from versions that have ended life in the past.
Here you will find an step by step guide how you can do an in place upgrade to Windows Server 2025 in video form from all the previous supported versions. Keep in mind that the moment this article is written the Windows Server 2025 is still in beta version and the in-place upgrade doesn’t offer the option to migrate apps and files. In the official release we expect to have this available. The technical procedure is the same as demonstrated in the video below with all the difference that you will have to click on the option to keep apps and files (the one that now is greyed out).
Personal Experience:
Testifying my personal experience, I was never a big fan of in-place upgrades. Many times, migrating from previous OS and applications without a clean install hides issues. Those issues might not be visible when an upgrade completes and become visible in the future after a newer update. So get an educated decision before you use in-place upgrades in your infrastructure. You should mandatorily have a full server backup before you start.
Key points:
- Windows Server 2025 supports upgrades from all 4 previous Windows Server versions.
- In-place upgrade in previous Windows Server versions has max 2 previous versions support.
Q&A:
You can upgrade to Windows Server 2025 from Windows Server 2012 R2 and later.
Yes, the procedure is identical for domain joined Servers too.
Conclusion:
Upgrade from several previous Windows Server versions is now possible. Choose your path to the latest Windows Server 2025 OS.
Hopefully the Windows Server 2025 in-place upgrade guide will help you get decisions for your next steps with your upgrade decisions related to Windows Server architecture. As backup is a vital point of this procedure, I have also written an article on backup helping protecting your data. You can give it a check here.
For detailed instructions on the migration path, check the infographic I created above or visit this official Windows Learn article from Microsoft.
If the above sounds confusing, very technical, or just time consuming for you current capacity, we are here to help Contact us by Clicking Here. We are helping businesses to stabilizing and optimizing their environments. We also offer monitoring as a service if you just want us to keep an eye and alert you if something has indications of the will stop working soon. Here is an article related to monitoring
 | About Alexios Pappas – Alexios Pappas has worked internally in IT Departments in multi-role technical and management positions for many years. In parallel, Alexios led IT multinational projects across several countries globally as an IT Freelancer. He repeatedly got Top Rated Plus distinction and also 100% satisfaction rate for over one and a half-decade, resulting from the Client’s feedback. Since 2015 he has been focused on informing and helping Businesses that want to improve and excel in their IT Section. |
