Always On VPN Security Updates September 2026

Microsoft released the September 2026 security updates today, which include numerous fixes affecting Always On VPN deployments. This month’s edition addresses vulnerabilities in Windows Server Routing and Remote Access (RRAS), VPN protocols such as Secure Socket Tunneling Protocol (SSTP) and Internet Key Exchange version 2 (IKEv2). The updates also include Active Directory Certificate Services (AD CS), a crucial supporting infrastructure service for Always On VPN.

RRAS

September 2026 Microsoft security updates include 8 CVEs for RRAS. Four are rated Critical, the most severe having a CVSS rating of 9.8.

RCEs

The following four CVEs are Remote Code Execution vulnerabilities. All are rated critical.

Privilege Escalation

The following two CVEs are RRAS privilege escalation vulnerabilities. All are rated Important.

Denial of Service

Finally, the last CVE addresses a denial-of-service vulnerability in RRAS.

VPN Protocols

The following section outlines vulnerabilities addressed in the September 2026 security updates affecting commonly used VPN protocols.

SSTP

The following four CVEs cover vulnerabilities in SSTP. One is rated critical with a CVSS score of 9.8. The rest are rated Important.

IKEv2

The following CVEs address vulnerabilities in the IKEv2 VPN protocol. All are rated important.

AD CS

Microsoft AD CS is commonly deployed to issue and manage certificates used for encryption and user and device authentication in Always On VPN deployments. The following four CVEs address vulnerabilities disclosed in AD CS. The first two are privilege escalation vulnerabilities, the third covers information disclosure, and the last addresses a tampering vulnerability. All are rated Important.

Summary

The September 2026 Microsoft security updates address several critical vulnerabilities affecting organizations that have deployed Microsoft Always On VPN. Administrators are encouraged to update their systems as soon as possible.

Additional Information

Microsoft September 2026 Security Updates

Always On VPN NPS and PEAP Vulnerabilities

The February 2023 security updates for Windows Server address multiple vulnerabilities that affect Microsoft Always On VPN administrators. This latest update addresses multiple critical and important vulnerabilities in the Network Policy Server (NPS), commonly used to perform RADIUS authentication for Always On VPN servers. Specifically, there are several Remote Code Execution (RCE) and Denial of Service (DoS) vulnerabilities with Protected Extensible Authentication Protocol (PEAP). PEAP with user authentication certificates is the authentication protocol of choice for Always On VPN user tunnel authentication.

Vulnerabilities

The following is a list of vulnerabilities in PEAP addressed in the February 2023 security update.

  • CVE-2023-21689Microsoft PEAP Remote Code Execution Vulnerability (critical)
  • CVE-2023-21690Microsoft PEAP Remote Code Execution Vulnerability (critical)
  • CVE-2023-21691Microsoft PEAP Information Disclosure vulnerability (important)
  • CVE-2023-21692Microsoft PEAP Remote Code Execution Vulnerability (critical)
  • CVE-2023-21695Microsoft PEAP Remote Code Execution Vulnerability (important)
  • CVE-2023-21701Microsoft PEAP Denial of Service Vulnerability (important)

Mitigation

Unauthenticated attackers can exploit the RCE vulnerabilities in PEAP on Microsoft Windows NPS servers. However, NPS servers should not be exposed directly to the Internet and would require an attacker to have access to the internal network already. However, administrators are advised to apply this update to their NPS servers as soon as possible. In addition, organizations that deploy the NPS role on enterprise domain controllers should update immediately.

Additional Information

February 2023 Update for Windows Server 2022 (KB5022842)

February 2023 Update for Windows Server 2019 (KB022840)

February 2023 Update for Windows Server 2016 (KB5022838)

Always On VPN Updates for RRAS and IKEv2

Always On VPN Updates for RRAS and IKEv2

Many users have reported connection stability issues using Windows Server 2019 Routing and Remote Access Service (RRAS) and the IKEv2 VPN protocol. Specifically, there have been reports of random disconnects for which the connection cannot be re-established for an extended period. At the same time, other VPN connections may work without issue.

KB5003703

Microsoft has identified an issue in RRAS where the RemoteAccess service enters DoS protection mode, limiting incoming IKEv2 connection attempts. They released an update on June 15 (OS Build 17763.2028) that addresses this issue. Previously, the only workaround was to restart the IKEEXT service, which was highly disruptive if performed during peak hours.

No More Files

In addition, this update includes another Always On VPN-related fix for Windows 10 1809 clients. An Always On VPN user tunnel connection may fail, with an error message stating, “There are no more files.” The problem can occur after an existing user’s certificate is automatically renewed.

Additional Information

Microsoft Update June 15, 2021 KB5003703 (OS Build 17763.2028)