Always On VPN Device Tunnel Fails to Connect Automatically

After the April 2024 Microsoft security updates were released, many Always On VPN administrators noticed that the device tunnel suddenly stopped connecting automatically for many, if not all, their endpoints.

Note: There were additional problems with the April 2024 security update that affected the Always On VPN device tunnel. Details here.

Troubleshooting

When this problem occurs, administrators can establish the device tunnel connection successfully if it is initiated manually. This indicates that there are no issues with the IKEv2 VPN connection or security configuration.

Subscription Activation

The root cause of this issue is related to a subscription activation issue broken in the April 2024 security updates. In this case, Windows 10/11 Enterprise Edition devices that were initially provisioned using Professional Edition and used a step-up upgrade (subscription activation) to Enterprise Edition are reverting to Professional Edition. The Always On VPN device tunnel requires Enterprise Edition to work correctly. Although you can deploy a device tunnel to Windows Professional, it will not connect automatically. It will, however, connect manually.

KB5040527

On July 25, 2024, Microsoft released a preview of updates (KB5040527), including a fix for this subscription activation issue. Administrators experiencing problems with Always On VPN device tunnels where their devices revert to Professional Edition can install this update to resolve this issue.

Additional Information

Always On VPN Device Tunnel Issue with the Microsoft April 2024 Security Update

Always On VPN Device Tunnel Status Indicator

Always On VPN Devcie Tunnel Only Deployment Considerations

Always On VPN Security Updates June 2024

The Microsoft security updates for June 2024 have now been published. Reviewing the list of bulletins shows three security updates of importance to Always On VPN administrators. Two affect the Windows Server Routing and Remote Access (RRAS) service, and one affects the Remote Access Connection Manager (RasMan) service. None of the updates are critical this month, which is good news.

RRAS

The following are the two security updates from this month’s cycle affecting Windows Server RRAS.

CVE-2024-30094 – Windows RRAS Remote Code Execution Vulnerability (Important)

CVE-2024-30095 – Windows RRAS Remote Code Execution Vulnerability (Important)

RasMan

The following security update affects the Remote Access Connection Manager (RasMan) service on Windows Server systems.

CVE-2024-30069 – Windows Remote Access Connection Manager Information Disclosure Vulnerability (Important)

Recommendations

None of the security vulnerabilities disclosed this month are critical and require local access to the system to take advantage of the exploit. However, administrators should update their systems as soon as possible.

Additional Information

Microsoft June 2024 Security Updates

Always On VPN April 2024 Security Updates

Microsoft has released its security updates for April 2024. This month, a few vulnerabilities are potentially impacting Always On VPN administrators. Specifically, three updates address issues with the Windows Server Routing and Remote Access Service (RRAS). In addition, vulnerabilities affect the Remote Access Connection Manager (RasMan) service, affecting both VPN servers and clients.

RRAS

Windows Server Routing and Remote Access (RRAS) has three security updates available this month. All three are Remote Code Execution (RCE) vulnerabilities but require user interaction to exploit the vulnerability. All three updates are rated as Important.

CVE-2024-26179

CVE-2024-26200

CVE-2024-26205

RasMan

In addition to the vulnerabilities in RRAS, Microsoft announced numerous updates for vulnerabilities discovered in the Remote Access Connection Manager (RasMan) service. These vulnerabilities are related to information disclosure via buffer overruns. These updates affect both Windows RRAS servers and Windows Always On VPN clients. All updates are rated as Important.

CVE-2024-26207

CVE-2024-26211

CVE-2024-26217

CVE-2024-26255

CVE-2024-28900

CVE-2024-28901

CVE-2024-28902

Recommendations

While none of these vulnerabilities are critical, Always On VPN administrators are urged to update their affected systems soon.

Additional Information

April 2024 Security Updates