Always On VPN IPsec Root Certificate Configuration Issue

Always On VPN Device Tunnel Status IndicatorWhen configuring a Windows Routing and Remote Access Service (RRAS) server to support Internet Key Exchange version 2 (IKEv2) VPN connections, it is essential for the administrator to define the root certification authority for which to accept IPsec security associations (SAs). Without defining this setting, the VPN server will accept a device certificate issued by any root certification authority defined in the Trusted Root Certification Authorities store. Details about configuring IKEv2 security and defining the root certification authority can be found here.

Multiple Root Certificates

Administrators may find that when they try to define a specific root certification authority, the setting may not be implemented as expected. This commonly occurs when there is more than one root certificate in the Trusted Root Certification Authorities store for the same PKI.

Always On VPN IPsec Root Certificate Configuration Issue

Certificate Selection

When running the PowerShell command Set-VpnAuthProtocol to define the root certification authority, PowerShell may ignore the administrator-defined certificate and choose a different one, as shown here. This will result in failed IPsec VPN connections from Windows 10 Always On VPN clients using IKEv2.

Always On VPN IPsec Root Certificate Configuration Issue

Certificate Publishing

This issue can occur when root certification authority certificates are published using Active Directory group policy. It appears that Windows prefers Active Directory group policy published certificates over those published directly in the Certification Authorities Container in Active Directory. To resolve this issue, remove any group policy objects that are publishing root certification authority certificates and ensure those root certificates are published in the Certification Authorities container in Active Directory.

PowerShell Script

A PowerShell script to configure this setting that can be found in my Always On VPN GitHub repository here. I have updated this script to validate the defined root certification authority certificate and warn the user if it does not match.

Additional Information

Set-Ikev2VpnRootCertificate.ps1 PowerShell script on GitHub

Windows 10 Always On VPN IKEv2 Security Configuration

Windows 10 Always On VPN IKEv2 Load Balancing and NAT

Windows 10 Always On VPN IKEv2 Features and Limitations

Windows 10 Always On VPN IKEv2 Fragmentation

Windows 10 Always On VPN IKEv2 Certificate Requirements

Always On VPN Updates for Windows 10 2004

Always On VPN Updates for Windows 10 2004Microsoft recently made available an update for Windows 10 2004 that includes many important fixes for outstanding issues with Windows 10 Always On VPN. KB4571744 (build 19041.488) addresses many challenges faced by Always On VPN administrators today, including the following.

TPM

This update addresses an issue that prevents hash signing from working correctly using the Microsoft Platform Crypto Provider for Trusted Platform Module (TPM). This issue can occur when administrators configure Always On VPN to use Protected Extensible Authentication Protocol (PEAP) with client certificate authentication using a FortiGate security device.

Sleep/Hibernate

This update also addresses issues with Windows 10 Always On VPN failing to automatically reconnect when resuming from sleep or hibernate. I’ve written about issues with Always On VPN and sleep/hibernate in the past. This is an issue that has plagued Always On VPN since its introduction, so let’s hope this finally provides some meaningful relief from this persistent problem.

Certificate Authentication

When both the Always On VPN device tunnel and user tunnel are provisioned to a Windows 10 clients, user tunnel connections may be authenticated using the machine certificate and not EAP/PEAP. This can result in connections that are not validated as intended, and allowing a user to bypass configured NPS policies, MFA requirements, or conditional access rules. This update includes a fix for this issue, restoring proper authentication for the user tunnel when the device tunnel is also provisioned.

Device and User Tunnel Coexistence

A bug that first appeared when Windows 10 2004 was introduced prevented a device tunnel and user tunnel Always On VPN connection from being established to the same VPN server if the user tunnel used Internet Key Exchange Version 2 (IKEv2). This update restores full functionality under those conditions.

Update KB4571744

To resolve these issues with Windows 10 Always On VPN as well as others, download and install update KB4571744 today. If you are experiencing any of these issues with releases of Windows 10 prior to 2004, look for updates for those build to come later this year.

Additional Information

September 3, 2020 – KB4571744 (OS Build 19041.488) Preview

Windows 10 Always On VPN Connection Issues after Sleep or Hibernate

Windows 10 Always On VPN Bug in Windows 10 2004

Always On VPN SSTP Certificate Binding Error

Always On VPN SSTP Certificate Binding ErrorWhen configuring a Windows Server with the Routing and Remote Access Service (RRAS) role to support Windows 10 Always On VPN connections, the administrator may encounter the following error message when installing or updating the TLS certificate used for Secure Socket Tunneling Protocol (SSTP) connections.

“The thumbprint (cert hash) of the certificate used for Secure Socket Tunneling Protocol (SSTP) is different than the certificate bound to the Web listener (HTTP.sys). Configure SSTP to use the default certificate or the certificate bound to SSL. You can configure web server applications to use the same certificate used by SSTP.”

Always On VPN SSTP Certificate Binding Error

IIS Binding

Most commonly this error can occur if an administrator mistakenly binds a TLS certificate directly in IIS. To resolve this problem, open the IIS management console (inetmgr.exe), navigate to the Default Web Site and click Bindings in the Actions section. Highlight the HTTPS binding and click Remove. Once complete, open an elevated command window and run the iisreset.exe command.

Always On VPN SSTP Certificate Binding Error

Netsh

In some instances, the administrator may find no certificate bindings in the IIS management console. However, a certificate binding may still be present. To confirm, open an elevated command window and run the following command.

netsh.exe http show sslcert

Always On VPN SSTP Certificate Binding Error

Remove existing certificate binding by running the following commands.

netsh.exe http delete sslcert ipport=0.0.0.0:443
netsh.exe http delete sslcert ipport=[::]:443

SSTP Configuration

When configuring SSTP in RRAS for Always On VPN, certificate assignment should always be performed using the Routing and Remote Access management console (rrasmgmt.msc). No changes are required to be made in the IIS management console for SSTP.

Additional Information

Windows 10 Always On VPN SSL Certificate Requirements for SSTP

Windows 10 Always On VPN SSTP Load Balancing with Citrix NetScaler ADC Load Balancer

Windows 10 Always On VPN SSTP Load Balancing with Kemp LoadMaster Load Balancer

Windows 10 Always On VPN SSTP Load Balancing with F5 BIG-IP Load Balancer