Always On VPN Security Updates July 2025

Patch Tuesday has arrived, and, unlike last month, it’s a busy month for Always On VPN administrators. The June 2025 Microsoft security updates address a whopping 16 (!) vulnerabilities in the Windows Routing and Remote Access Service (RRAS). Notably, DirectAccess administrators are once again impacted by a critical vulnerability in the Windows KDC Proxy Service (KPSSVC) this month.

RRAS

As stated previously, this month’s update addresses 16 unique CVEs in Windows Server RRAS. All are memory-related buffer overflows and out-of-bounds reads, indicating that a security researcher was recently probing for vulnerabilities in RRAS.

While all the above CVEs are Remote Code Execution (RCE) and Information Disclosure vulnerabilities, none are rated as Critical; all are rated as Important. This means exploitation is unlikely, but administrators are encouraged to update as soon as possible.

KDC Proxy

This month’s security update includes another Critical RCE in the Windows KDC Proxy Service (KPSSVC).

The KDC Proxy is enabled by default when DirectAccess is configured. By design, this means the service is exposed to the public Internet, posing a significant risk to organizations using DirectAccess for secure remote access. Administrators are urged to update their systems immediately to avoid compromise.

Additional Information

Microsoft July 2025 Security Updates

Always On VPN Security Updates June 2025

Patch Tuesday is upon us again; thankfully, it’s a light month of Always On VPN administrators. The Microsoft monthly security updates for June 2025 include just a few Windows Routing and Remote Access Service (RRAS) fixes. In addition, an update is available for a vulnerability in the Windows Remote Access Connection Manager. Significantly, DirectAccess administrators are affected this month by a vulnerability identified in the Windows KDC Proxy Service (KPSSVC).

RRAS Updates

The Microsoft security updates for June 2025 address the following CVEs for Windows Server RRAS.

Both RRAS CVEs are Remote Code Execution (RCE) vulnerabilities with max severity ratings of Important.

Remote Access Connection Manager

A security vulnerability in the Windows Remote Access Connection Manager is addressed with the following CVE.

An attacker exploiting this vulnerability could elevate local access privileges.

KDC Proxy

This critical vulnerability affects those organizations still supporting Microsoft DirectAccess in their environments.

This CVE addresses an RCE in the KDC Proxy Service (KPSSVC) that could allow an attacker to execute arbitrary code over the network. DirectAccess administrators are encouraged to apply this update as soon as possible.

Additional Information

Microsoft June 2025 Security Updates

Always On VPN Authentication Failure After February 2025 Security Update

Microsoft introduced changes to Windows domain controllers in the February 2025 security update that may result in authentication failures for Always On VPN user tunnel connections. If you suddenly find that all your Always On VPN user tunnel connections fail, additional changes may be required to resolve the issue.

Authentication Failure

Administrators may find that Always On VPN connections fail after applying the February 2025 Microsoft security updates. Specifically, users may receive the following warning message.

“The remote access connection completed, but authentication failed because the certificate that authenticates the client to the server is not valid. Ensure that the certificate used for authentication is valid.”

Error 853

Administrators will also find a corresponding event log entry with event ID 20227 from the RasClient source with the following error message.

“The user <username> dialed a connection named <connection name> which has failed. The error code returned on failure is 853.”

NPS Events

The event log on the NPS server will also record event ID 6273 from the Microsoft Windows security auditing source with the following error message.

“Network Policy Server denied access to a user.”

The authentication details of the event include Reason Code 16 with the following reason.

“Authentication failed due to a user credentials mismatch. Either the user name provided does not map to an existing user account or the password was incorrect.”

DC Events

If the issue is related to changes implemented to domain controllers in the February 2025 security update, administrators will also find a corresponding event log entry on a domain controller with event ID 39 from the Kerberos-Key-Distribution-Center source with the following error message.

“The Key Distribution Center (KDC) encountered a user certificate that was valid but could not be mapped to a user in a secure way (such as via explicit mapping, key trust mapping, or a SID). Such certificates should either be replaced or mapped directly to the user via explicit mapping.”

Root Cause

The above conditions indicate that a user attempted to authenticate to the VPN with a certificate that was not strongly mapped. Most likely, the certificate was issued using Microsoft Intune with SCEP or PKCS. This results from changes made to domain controllers in the February 2025 security update that requires certificates used for Active Directory authentication to be strongly mapped. Until now, domain controllers allowed access and only logged an event in the event log when a certificate did not include strong certificate mapping. The February 2025 security update now enforces strong certificate mapping, and authentication requests will fail without it.

Resolution

Administrators must issue new certificates that are strongly mapped to resolve this issue. For certificates issued with PKCS, changes are required on the Intune Certificate Connector server before re-issuing. For certificates issued with SCEP, changes to the device configuration policy are required. See the post Strong Certificate Mapping for Intune PKCS and SCEP Certificates for more details.

Workaround

Re-issuing certificates takes time. To restore connectivity immediately, administrators can implement the following registry settings on all domain controllers to switch back to audit mode and allow authentication without strong certificate mapping.

Key: HKLM:\SYSTEM\CurrentControlSet\Services\Kdc
Name: StrongCertificateBindingEnforcement
Type: DWORD
Value: 1

I recommend deploying this setting via GPO assigned to the Domain Controllers OU. However, you can also implement this change using PowerShell if necessary.

New-ItemProperty -Path ‘HKLM:\SYSTEM\CurrentControlSet\Services\Kdc’ -Name ‘StrongCertificateBindingEnforcement’ -PropertyType DWORD -Value 1 -Force

Additional Information

Strong Certificate Mapping for Intune PKCS and SCEP Certificates

Strong Certificate Mapping Enforcement February 2025

Certificate-Based Authentication Changes and Always On VPN

Intune Strong Certificate Mapping Error

Strong Certificate Mapping Error with PKCS