Microsoft’s Latest Windows Updates Cause Major Issues with Always On VPN Connections
IT administrators around the world are facing a major headache after Microsoft’s latest set of security updates for Windows 11 caused Always On VPN connections to malfunction. The issue, which affects both home and enterprise users, has left many struggling to connect to their organization’s network via the remote access solution.
Always On VPN is a secure connection technology that allows devices to establish a seamless and automatic tunnel back to the corporate network whenever they’re connected to the internet. It replaces older DirectAccess technology and works with various types of devices, including domain-joined, non-domain-joined, and Microsoft Entra ID–joined systems. The solution provides robust security features such as multi-factor authentication (MFA) and supports modern VPN protocols like IKEv2 and SSTP.
However, after installing the September 2026 Windows updates, users may experience issues when attempting to connect via Always On VPN. According to a service alert from Microsoft, the problem occurs when the VPN is configured to automatically try another connection method if the initial attempt fails. This can result in affected connections remaining stuck in a “Connecting” state or repeatedly trying to establish a link without success.
In some cases, subsequent connection attempts may display an error message stating that the specified port is already in use. While Microsoft acknowledges the issue and is working on a permanent solution, it has shared a temporary fix for affected customers. To mitigate the problem, IT administrators are advised to change the Always On VPN profile from automatic protocol selection to a single protocol, either SSTP or IKEv2 only.
This month’s cumulative updates have been linked to multiple other issues affecting Windows users, including problems with Hyper-V, Remote Desktop Services, and USB audio. Microsoft has released emergency updates to address some of these issues but is still working on fixing others. The latest problem underscores the importance of thorough testing and validation before deploying security updates in large-scale environments.
For those affected by this issue, it’s essential to be aware that choosing a single protocol may impact system performance or security requirements. IT administrators should carefully evaluate their environment, security, and deployment needs before implementing this temporary fix. As Microsoft continues to work on a permanent solution, users can take steps to prepare for potential disruptions in their Always On VPN connections.
In light of these issues, it’s crucial that organizations prioritize robust testing procedures and validation processes when deploying security updates. By doing so, they can minimize the risk of unexpected problems and ensure business continuity. For home users, staying informed about updates and taking proactive measures to maintain system stability is also vital for avoiding potential disruptions.
Source: Bleeping Computer — 2026-09-23