Microsoft Warns of Always On VPN Issues After September Windows Updates
Microsoft has notified IT administrators that Always On VPN connections may be disrupted after installing the September 2026 Windows 11 security updates.
Always On VPN is a remote access solution that replaces legacy DirectAccess technology and works with domain-joined, non-domain-joined, and Microsoft Entra ID, joined devices.
The issue can occur when the VPN is configured to automatically try another connection method if the initial connection fails, according to Microsoft. Affected users may experience issues when attempting to connect to their organization's enterprise network via Always On VPN.
Microsoft has shared a temporary fix for affected customers, which requires choosing one of two VPN tunneling protocols: SSTP only or IKEv2 only.
This is not the first issue related to this month's cumulative updates; Microsoft has released emergency updates to address Hyper-V issues, Remote Desktop Services failures, and USB audio problems triggered by the September 2026 updates.