Windows 11 25H2 known issues causing upgrade nightmare

Windows 11 25H2 inherits many of the same bugs from 24H2 and adds two confirmed issues, including IIS websites might fail to load.
When upgrading, proceed cautiously with backups and check Microsoft’s Health Dashboard.

UPDATED 10/20/2025: Microsoft released the Windows 11 2025 Update (version 25H2) on September 30, 2025. However, several known issues may still prevent your device from upgrading. This latest feature update is a small release that doesn’t introduce new features if you’re upgrading from version 24H2.

However, it doesn’t mean that a small update can’t cause issues, as every release has its challenges. The complete list of known issues for Windows 11 25H2 is available on the Microsoft Health Dashboard page. At the time of writing, only a few problems are currently blocking the upgrade.

For example, Microsoft has confirmed a problem with USB mouse and keyboard not working in the recovery environment (this issue has been resolved), and websites might fail to load using IIS.

What are the known issues on Windows 11 25H2

Here’s the list of confirmed issues blocking the upgrade to the Windows 11 2025 Update:

(Confirmed) IIS websites might fail to load: Server-side applications that rely on HTTP.sys may experience issues with incoming connections.

Resolved or mitigated issues

(Resolved) USB mouse and keyboard not working in the Windows Recovery Environment (WinRE): This issue affects USB devices only within WinRE after installing update KB5066835. This problem has been resolved with the Out-of-band update KB5070773.
(Resolved) Smartcard authentication issues might occur with the October 2025 Windows update: This issue is related to a security change introduced for strengthening Windows Cryptographic Services.
(Mitigated) Problems playing protected content in some Blu-ray/DVD/Digital TV applications: Certain apps are unable to display or record live TV or play Digital Rights Management (DRM) protected content.
(Mitigated) Updates installed via WUSA might fail if installed from a shared folder: This issue might occur when installing an update from a network folder containing multiple .msu files.

If your device is stuck and getting a Blue Screen of Death, you can mitigate the problem by uninstalling Windows 11 25H2 until the problem has been resolved. If you’re planning to upgrade to version 25H2, you can use these recommendations before proceeding to avoid problems.

If a problem is identified that could negatively affect devices, the company will place a safeguard hold to prevent those computers from downloading the update until the issue has been resolved.

If you are still deciding whether to upgrade your computer now or wait until later, this guide will help you make an informed decision.