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Microsoft: October Updates Did Not Fix Windows VPN Issues

Microsoft has clarified that a bug impacting Always On VPN connections was mistakenly marked as resolved in the October 2026 cumulative updates, leaving IT administrators to rely on temporary workarounds while a permanent fix is developed.

Radwan AbdulhadiEditor and technology writer

Published: October 22, 2026 · Updated: October 22, 2026 · 3 min read

Microsoft: October Updates Did Not Fix Windows VPN Issues — Image: BleepingComputer

Always On VPN Bug Mistakenly Flagged as Resolved

Microsoft says it mistakenly flagged a bug causing Always On VPN connection issues as fixed in the October 2026 Windows 11 cumulative updates. The issue affects Always On VPN, which replaced the legacy DirectAccess technology and supports domain-joined, non-domain-joined, and Microsoft Entra ID–joined devices running Windows 10, Windows 11, and Windows Server.

The problem runs in the background and establishes secure tunnels back to a user's corporate network whenever their device connects to the internet. According to details shared in a service alert sent to IT administrators, the glitch was triggered on systems running Windows 11 24H2 and later after installing the September 2026 security updates when the initial Always On VPN connection failed during automatic protocol selection with IKEv2 and SSTP.

Connection Failures and Status Correction

When automatic protocol selection or protocol fallback was configured, affected VPN connections could remain stuck in a connecting state or fail to connect entirely after an initial attempt failed. In some cases, subsequent connection attempts could display the error message indicating that the specified port is already in use.

After releasing the October 2026 Patch Tuesday Windows 11 cumulative updates, Microsoft initially marked the bug as resolved. However, in a Tuesday update it clarified that the issues were not actually addressed and that a proper fix would ship later.

The company addressed the miscommunication in a service alert sent to IT admins, noting that the disclosure was mistakenly updated to resolved status on October 13, 2026, and has since been returned to a mitigated status while a permanent resolution is prepared for an update coming in the next few weeks.

Temporary Mitigation and Workarounds

While Microsoft continues working on a permanent solution, the company has shared a temporary fix that requires affected customers to choose a single VPN tunneling protocol to bypass the connection errors.

IT administrators can mitigate this issue by changing the Always On VPN profile from automatic protocol selection to a single protocol, choosing either SSTP only or IKEv2 only depending on their environment and configuration. Organizations should carefully select the protocol based on their specific environment, security policies, and deployment requirements.

Broader Impact of Recent Windows Updates

The September cumulative updates have been linked to multiple other problems affecting both home and enterprise Windows users. Days after last month's Patch Tuesday, Microsoft released emergency out-of-band updates to fix Hyper-V issues, Remote Desktop Services failures, and USB audio problems.

Among the additional reported complications were host folder share availability concerns alongside Remote Desktop Services failures and hardware-specific USB audio difficulties.

Additionally, Microsoft shared a temporary workaround for an authentication issue that blocked certain Windows domain login capabilities and noted ongoing work to address bugs impacting built-in features like File History backup.