Microsoft: September Windows updates break Always On VPN connections
Microsoft September 2026 updates cause Always On VPN connection failures.
Microsoft has alerted IT administrators that its September 2026 security updates for Windows 11 may cause Always On VPN connections to fail. The issue occurs when the VPN is configured for automatic protocol selection and attempts to switch between IKEv2 and SSTP. A temporary workaround involves manually selecting a single protocol (SSTP or IKEv2) in the VPN profile.
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The lesson from this incident
Full lessonMicrosoft's September 2026 Windows 11 security updates introduced a regression that disrupts Always On VPN connections configured for automatic protocol selection, specifically when switching between IKEv2 and SSTP. This highlights the inherent risk of deploying security patches without adequate pre-production testing, particularly for critical remote access infrastructure. Organizations relying on Always On VPN for secure remote workforce connectivity may find employees suddenly unable to connect, creating both productivity and security gaps. The fact that a manual workaround exists underscores the importance of having documented fallback procedures before patch deployment. Patch management must account not only for vulnerability remediation but also for functional regression in security-critical services.
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