I'm currently trying to upgrade my system from Windows Server 2019 to Windows Server 2025. I've ensured that my current OS is fully updated and I'm using the official Windows Server 2025 ISO downloaded from Microsoft's website. My setup includes choosing the right edition, which is Windows Server 2025 Standard (Desktop Experience), and my language is set to English (United States). However, when I reach the 'Choose what to keep' screen during the installation process, the option to 'Keep files, settings, and apps' is grayed out. The only option available is 'Nothing,' meaning a clean installation. I'm wondering if anyone has faced this issue or has insight into why the in-place upgrade isn't allowing me to keep my files and settings. Thanks for your help!
5 Answers
Just a heads up, if you're trying to use a non-licensed or Eval version of the Server 2025 ISO, that could definitely be the cause of your issue. You won't be able to upgrade from a licensed server using an Eval copy.
As a workaround, you could set up a temporary Windows Server 2019 machine and try the upgrade there to see if you get the same result. That might help pinpoint any issues.
It might also be due to some server roles that aren't supported in the new version. Have you checked if all your current roles are compatible?
If that's the case, what are my options? Do I need to wipe everything and start fresh?
If you've purchased the full version of Server 2025, make sure you're using the proper ISO from your M365 Admin center, not the evaluation version. That could resolve your upgrade issues.
Are you sure the language setting on the installation media matches your current OS? Sometimes mismatches there can cause options to be grayed out.
Yeah, I checked. Everything matches, but I still can't select that option.
Good point! Make sure you have the correct licensing version available.