Microsoft has recently acknowledged a significant oversight regarding its Always On VPN feature, which has been experiencing connection issues. The company initially indicated that these problems had been resolved in the October 2026 cumulative updates for Windows 11. However, a subsequent update revealed that the issues persist, and a true fix is still forthcoming.
Always On VPN serves as a modern replacement for the older DirectAccess technology, catering to a wide range of devices, including those that are domain-joined, non-domain-joined, and those utilizing Microsoft Entra ID. This feature operates seamlessly in the background, establishing secure connections to corporate networks whenever a device connects to the internet.
Mistakenly marked as resolved
The trouble began when Microsoft issued a service alert to IT administrators in late September, acknowledging that the connection issues were triggered on systems running Windows 11 24H2 and later versions after the installation of September 2026 security updates. These issues primarily affected users employing automatic protocol selection with IKEv2 and SSTP, leading to VPN connections that either remained stuck in a “Connecting” state or failed entirely after an initial attempt.
In a rather perplexing turn of events, after the release of the October 2026 Patch Tuesday updates, Microsoft prematurely marked the bug as resolved. A recent service alert clarified that this status was mistakenly assigned and has since been reverted to “Mitigated.” The company has committed to releasing a proper resolution in the coming weeks and has expressed its apologies for any confusion caused.
While a permanent fix is in the works, Microsoft has provided a temporary workaround for affected users. IT administrators are advised to adjust their Always On VPN profiles by selecting a single tunneling protocol—either SSTP or IKEv2—rather than relying on automatic protocol selection. This adjustment should be made based on the specific environment and security requirements of the organization.
The September cumulative updates have not only been linked to the Always On VPN issues but have also caused a range of other problems for both home and enterprise users. Following the last Patch Tuesday, Microsoft was compelled to release emergency out-of-band updates to address critical issues, including problems with Hyper-V, Remote Desktop Services, and USB audio functionalities. Additionally, a temporary workaround was shared for an issue preventing some Windows 11 users from logging in with valid domain credentials, alongside ongoing efforts to rectify a bug affecting the built-in File History backup feature.
