Microsoft Windows updates break authentication on systems with duplicate SIDs
Service Disruption
Summary
Hide ▲
Show ▼
Microsoft Windows updates released since August 29, 2025 are breaking Kerberos and NTLM authentication on systems with duplicate SIDs, disrupting Remote Desktop access and causing login failures on Windows 11 24H2, Windows 11 25H2, and Windows Server 2025. The change blocks authentication handshakes between cloned devices that share the same Security Identifier. Administrators are being told to rebuild affected systems with supported imaging methods or use a temporary Group Policy workaround.
Related Happenings
Microsoft Windows Server 2025 and Windows 11 23H2 BitLocker recovery fix
Security Patch Release
H score15
First: 11.06.2026 11:44
Last: 11.06.2026 11:44
Sources 1
About this happening:
Microsoft shipped **KB5094125** for **Windows Server 2025** and **KB5093998** for **Windows 11 23H2** to fix a **BitLocker recovery** bug tied to the **April 2026 security update*...
Microsoft Windows Server 2025 and Windows 11 23H2 BitLocker recovery fix
Security Patch ReleaseAbout this happening: Microsoft shipped **KB5094125** for **Windows Server 2025** and **KB5093998** for **Windows 11 23H2** to fix a **BitLocker recovery** bug tied to the **April 2026 security update*...
Microsoft BitLocker recovery prompt workaround
Advisory/Mitigation
H score25
First: 09.06.2026 21:35
Last: 09.06.2026 21:35
Sources 1
About this happening:
Microsoft issued a **temporary workaround** for **BitLocker recovery prompts** on some **Windows** systems after recent updates. The issue affects devices configured with a **BitL...
Microsoft BitLocker recovery prompt workaround
Advisory/MitigationAbout this happening: Microsoft issued a **temporary workaround** for **BitLocker recovery prompts** on some **Windows** systems after recent updates. The issue affects devices configured with a **BitL...
Microsoft My Sign-Ins MFA outage
Service Disruption
H score25
First: 01.06.2026 14:40
Last: 01.06.2026 14:40
Sources 1
About this happening:
**Microsoft** is dealing with an **ongoing outage** that is blocking some users from setting up **multi-factor authentication (MFA)** and accessing **My Sign-Ins**. Affected users...
Microsoft My Sign-Ins MFA outage
Service DisruptionAbout this happening: **Microsoft** is dealing with an **ongoing outage** that is blocking some users from setting up **multi-factor authentication (MFA)** and accessing **My Sign-Ins**. Affected users...
Microsoft Windows Server 2016 domain controller discovery failure after KB5087537
Service Disruption
H score0
First: 26.05.2026 10:41
Last: 26.05.2026 10:41
Sources 1
About this happening:
Microsoft confirmed a **known issue** in **Windows Server 2016** after **KB5087537** that can prevent **domain controller discovery**, disrupting administrative operations and app...
Microsoft Windows Server 2016 domain controller discovery failure after KB5087537
Service DisruptionAbout this happening: Microsoft confirmed a **known issue** in **Windows Server 2016** after **KB5087537** that can prevent **domain controller discovery**, disrupting administrative operations and app...
Windows 10 KB5087544 extended security update
Security Patch Release
H score15
First: 12.05.2026 21:58
Last: 12.05.2026 21:58
Sources 1
About this happening:
**Microsoft** released **Windows 10 KB5087544** for **Windows 10 ESU/LTSC systems**, addressing **May 2026 Patch Tuesday vulnerabilities** and a **Remote Desktop warnings** issue....
Windows 10 KB5087544 extended security update
Security Patch ReleaseAbout this happening: **Microsoft** released **Windows 10 KB5087544** for **Windows 10 ESU/LTSC systems**, addressing **May 2026 Patch Tuesday vulnerabilities** and a **Remote Desktop warnings** issue....
Timeline
-
21.10.2025 19:56 1 articles · 7mo ago
Windows updates add SID checks that block duplicate-SID authentication
Mitigation Patch UpdateWindows updates released on and after August 29, 2025 add security protections that enforce checks on Security Identifiers, blocking authentication handshakes when cloned Windows installations share duplicate SIDs and were not prepared for imaging with Sysprep.
Show sources
- Microsoft: Recent Windows updates cause login issues on some PCs — www.bleepingcomputer.com — 21.10.2025 19:56
-
21.10.2025 19:56 2 articles · 7mo ago
Microsoft confirms duplicate-SID authentication failures and gives workarounds
Initial DisclosureMicrosoft confirmed in a support document published on Tuesday that Kerberos and NTLM authentication can fail across devices with duplicate SIDs, producing failed logins, access denied errors, SEC_E_NO_CREDENTIALS entries, and broken Remote Desktop connections on Windows 11 24H2, Windows 11 25H2, and Windows Server 2025. Administrators are told to rebuild duplicated systems with supported cloning methods or temporarily install and configure a special Group Policy obtained through Microsoft Support for business.
Show sources
- Microsoft: Recent Windows updates cause login issues on some PCs — www.bleepingcomputer.com — 21.10.2025 19:56
- Microsoft: Recent Windows updates cause login issues on some PCs — www.bleepingcomputer.com — 21.10.2025 19:56