If you are repeatedly prompted for authentication credentials after updating to Microsoft Windows 11 or Windows Server 2025, this could be the reason.
SOPA Images/LightRocket via Getty Images, comes more bad news. Microsoft has confirmed another Windows update issue, this time impacting Windows 11 and Windows Server users, that leads to the repeated prompting for authentication credentials, the failure of valid credentials, and remote desktop connections.
Here’s what you need to know and do.Microsoft is continually evolving the security protections available to users of the Windows operating systems, as evidenced in the recent announcement of new functionality to helpfrom malicious applications and actors threatening accounts. Sometimes, these updates can cause issues, even through they are ultimately there to enhance security rather than make your life miserable for no reason. Such would appear to be the case with the latest confirmation from Microsoft that “added security protections that enforce checks on Security IDs” put into place withexplained that users “might experience Kerberos and New Technology LAN Manager authentication failures across devices that have duplicate Security IDs.”These NTLM and SID issues are impacting users of Windows 11, version 24H2, Windows 11, version 25H2, and Windows Server 2025 following the August 29 update. This is caused by those aforementioned security protections, which, Microsoft confirmed, “enforce checks on SIDs, causing authentication to fail when devices have duplicate SIDs.” This is a good thing. Such duplicate SIDs are often created when performing “unsupported cloning or duplication of a Windows installation without running Sysprep.” SID uniqueness, enabled by Sysprep, is now a mandatory requirement for those Windows versions post-update. Without the new enforcements, it was possible for an unauthorized user to potentially get access to restricted files that were accessible on the duplicated SID system. “This design change blocks authentication handshakes between such devices,” Microsoft said, adding that “devices containing duplicate SIDs will need to be
Windows 11 Windows Server NTLM Kerberos Windows Authentication Failure Windows Server 2025 25H2 Windows Update Warning Windows Security Warning
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