Microsoft Windows Updates Break VPN Connections
September 2026 updates cause issues with Always On VPN, Microsoft provides temporary fix while working on permanent solution
Microsoft's September 2026 Windows updates have caused issues with Always On VPN connections, affecting users who have installed the updates and are trying to connect to their organization's enterprise network via Always On VPN.
The issue can occur when the VPN is configured to automatically try another connection method if the initial connection fails. Affected VPN connections might remain in a 'Connecting' state or repeatedly attempt to connect without succeeding. Subsequent connection attempts might also display the error: 'The specified port is already in use.'
Always On VPN is a remote access solution available on Windows 10, Windows 11, and Windows Server, which establishes a secure tunnel back to the corporate network automatically whenever a device connects to the internet. It supports modern VPN protocols like IKEv2 and SSTP, plus multi-factor authentication (MFA) for better security.
IT administrators can mitigate this issue by changing the Always On VPN profile from automatic protocol selection to a single protocol, either SSTP only or IKEv2 only. This temporary fix allows users to work around the issue while Microsoft works on a permanent solution.
## What happens next Microsoft is working to address the issue and has already released emergency updates to fix other problems triggered by the September 2026 updates, including Hyper-V issues, Remote Desktop Services failures, and USB audio problems. The company is also working to resolve another issue that blocks some Windows 11 users from logging in with valid domain credentials.
The disruption to Always On VPN connections is significant, as it affects users who rely on the service to connect to their organization's enterprise network remotely. The issue highlights the importance of testing and validating updates before they are rolled out to ensure that they do not cause unintended consequences. As Microsoft works on a permanent solution, affected users can use the temporary fix to maintain their VPN connections.
