Microsoft finally fixes VPN issues caused by September updates
Microsoft has resolved Always On VPN connection failures triggered after installing the September 2026 Windows 11 security updates.
Microsoft has resolved Always On VPN connection failures triggered after installing the September 2026 Windows 11 security updates.
The Always On VPN remote access solution runs in the background and establishes secure tunnels back to the user's corporate network when their devices connect to the Internet.
It has 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.
On Wednesday, Microsoft confirmed that this issue has finally been fixed for users who installed this month's KB5127936 preview update .
The October 2026 preview update also fixes a known issue preventing non-admin users from connecting to devices via Remote Desktop when the Administrator protection security feature is enabled after installing the September 2026 Windows 11 non-security preview update (or Windows updates released since then).
The Blue Report 2026 measures defenses technique by technique across 338 million simulations run in customer production environments.
The company first acknowledged it in a service alert sent to IT administrators in late September, saying the Always On VPN failures were triggered on Windows 11 systems by the September 2026 security updates when using automatic protocol selection with IKEv2 and SSTP.
When automatic protocol selection or protocol fallback was configured, affected VPN connections could remain stuck in a Connecting state or fail to connect after an initial connection attempt failed.
In some cases, subsequent connection attempts could display the error, 'The specified port is already in use.' Microsoft also provides a temporary fix for users who don't want to install the preview update and would rather wait for next month's Patch Tuesday cumulative updates.
This requires admins to choose one of two tunneling protocols to prevent Always On VPN failures on affected devices.
Microsoft fixes Remote Desktop failures caused by recent Windows updates
Microsoft has previously mistakenly flagged this known issue as fixed in the October 2026 Windows 11 cumulative updates.
What happened
Microsoft has resolved Always On VPN connection failures triggered after installing the September 2026 Windows 11 security updates.
The Always On VPN remote access solution runs in the background and establishes secure tunnels back to the user's corporate network when their devices connect to the Internet.
It has 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.
What changed
On Wednesday, Microsoft confirmed that this issue has finally been fixed for users who installed this month's KB5127936 preview update .
The October 2026 preview update also fixes a known issue preventing non-admin users from connecting to devices via Remote Desktop when the Administrator protection security feature is enabled after installing the September 2026 Windows 11 non-security preview update (or Windows updates released since then).
The Blue Report 2026 measures defenses technique by technique across 338 million simulations run in customer production environments.
Who is affected
The company first acknowledged it in a service alert sent to IT administrators in late September, saying the Always On VPN failures were triggered on Windows 11 systems by the September 2026 security updates when using automatic protocol selection with IKEv2 and SSTP.
When automatic protocol selection or protocol fallback was configured, affected VPN connections could remain stuck in a Connecting state or fail to connect after an initial connection attempt failed.
Why it matters
In some cases, subsequent connection attempts could display the error, 'The specified port is already in use.' Microsoft also provides a temporary fix for users who don't want to install the preview update and would rather wait for next month's Patch Tuesday cumulative updates.
This requires admins to choose one of two tunneling protocols to prevent Always On VPN failures on affected devices.
Technical details
Microsoft fixes Remote Desktop failures caused by recent Windows updates
Response
Microsoft has previously mistakenly flagged this known issue as fixed in the October 2026 Windows 11 cumulative updates.
Attribution
BleepingComputer: Microsoft has resolved Always On VPN connection failures triggered after installing the September 2026 Windows 11 security updates.
What to watch next
Watch for revised vendor guidance, fixed versions and mitigation updates.