Always On VPN Users Prompted for Certificate

Always On VPN Users Prompted for CertificateWhen deploying Windows 10 Always On VPN using Protected Extensible Authentication Protocol (PEAP) authentication with client certificates, administrators may find the VPN connection does not establish automatically. In this specific scenario the client is prompted to select a certificate to use to authenticate to the VPN server.

Always On VPN Users Prompted for Certificate

Multiple Certificates

This can occur when certificates from multiple Certification Authorities (CAs) are issued to the user that include the Client Authentication Enhanced Key Usage (EKU). When this happens, the user is forced to select the correct certificate to use for VPN authentication.

Clearly this is less than ideal, as it not only breaks the seamless and transparent nature of Always On VPN, the user may select the wrong certificate resulting in authentication failure. Ideally the client should be configured to select the correct certificate without user interaction.

Certificate Selection

Follow the steps below to configure automatic certificate selection for VPN authentication.

  1. On a VPN client, right-click the Always On VPN connection and choose Properties.
  2. Select the Security tab.
  3. In the Authentication section click Properties below Use Extensible Authentication Protocol (EAP).
  4. In the Select Authentication Method section click Configure.
  5. In the When connecting section click Advanced.
  6. Check the box next to Certificate Issuer.
  7. Select the root CA used to issue client authentication certificates for VPN authentication.
  8. Click Ok four times to save the configuration.

Always On VPN Users Prompted for Certificate

Once complete, export the EAP configuration to XML from the VPN client and paste the new settings in Intune or in your custom ProfileXML.

Certificate Purpose

By default, a client certificate requires only the Client Authentication EKU to establish a VPN connection. In some cases, this may not be desirable. For example, consider a deployment where Client Authentication certificates are issued to all users for Wi-Fi authentication. Depending on the Network Policy Server (NPS) configuration, these certificates may also be used to authenticate to the VPN.

VPN Specific Certificate

Follow the steps below to create a user authentication certificate template to be used exclusively for VPN authentication.

Certificate Template

  1. On the CA server, open the Certificate Templates management console (certtmpl.msc).
  2. Right-click the certificate template configured for VPN authentication and choose Properties.
  3. Select the Extension tab.
  4. Highlight Application Policies and click Edit.
  5. Click Add.
  6. Click New.
  7. Enter a descriptive name for the new application policy.
  8. Copy the Object identifier for later use and click Ok four times to save the configuration.

    Always On VPN Users Prompted for Certificate

  9. If certificate autoenrollment is configured and the certificate is already provisioned to users, right-click the certificate template and choose Reenroll All Certificate holders.

Client Configuration

  1. On the VPN client, follow the steps outlined previously to configure certificate selection.
  2. In addition to choosing a certificate issuer, select Extended Key Usage (EKU).
  3. Uncheck All Purpose.
  4. Select Client Authentication and the following EKUs.
  5. Click Add.
  6. Click Add once more.
  7. Enter the name of the custom EKU policy created previously.
  8. Enter the custom EKU object identifier copied previously from the custom policy.

    Always On VPN Users Prompted for Certificate

  9. Click Ok twice.
  10. Uncheck AnyPurpose and the following EKUs.
  11. Click Ok four times to save the configuration.

Always On VPN Users Prompted for Certificate

Once complete, export the EAP configuration to XML from the VPN client and paste the new settings in Intune or in your custom ProfileXML.

Additional Information

Windows 10 Always On VPN Clients Prompted for Authentication when Accessing Internal Resources

Get-EapConfiguration PowerShell Script on GitHub

Windows 10 Always On VPN Hands-On Training

Always On VPN Clients Prompted for Authentication when Accessing Internal Resources

Always On VPN Clients Prompted for Authentication when Accessing Internal ResourcesWhen deploying Windows 10 Always On VPN using Protected Extensible Authentication Protocol (PEAP) with client authentication certificates, the administrator may encounter a scenario in which the user can establish a VPN connection without issue, but when accessing internal resources they are prompted for credentials and receive the following error message.

“The system cannot contact a domain controller to service the authentication request. Please try again later.”

Always On VPN Clients Prompted for Authentication when Accessing Internal Resources

Resolution

This can occur if one or more domain controllers in the enterprise have expired or missing domain controller authentication certificates. To ensure seamless single sign-on to internal resources, ensure that all domain controllers have a certificate issued by the internal certification authority (CA) that includes the Server Authentication (1.3.6.1.5.5.7.3.1) and Smart Card Logon (1.3.6.1.4.1.311.20.2.2) Enhanced Key Usage (EKU) at a minimum.

Always On VPN Clients Prompted for Authentication when Accessing Internal Resources

Additional Information

Windows 10 Always On VPN Certificate Requirements for IKEv2

Windows 10 Always On VPN Hands-On Training

Always On VPN and Azure MFA ESTS Token Error

Always On VPN and Azure MFA ESTS Token ErrorConfiguring Multifactor Authentication (MFA) is an excellent way to ensure the highest level of assurance for Always On VPN users. Azure MFA is widely deployed and commonly integrated with Windows Server Network Policy Server (NPS) using the NPS Extension for Azure MFA. Azure MFA has a unique advantage over many other MFA providers in that it supports MFA when using Protected Extensible Authentication Protocol (PEAP). This makes Azure MFA the solution of choice for integrating with Windows 10 Always On VPN deployments using client certificate authentication, a recommended security configuration best practice.

NPS Configuration

Installing and configuring the NPS extension for Azure MFA is straightforward. Configuration guidance from Microsoft can be found here.

Connection Issues

After installing the NPS extension for Azure MFA, administrators may find that Always On VPN connections fail and the user is never challenged for authentication. The connection eventually times out and returns the following error message.

“A connection to the remote computer could not be established, so the port used for this connection was closed.”

Always On VPN and Azure MFA ESTS Token Error

In addition, the Application event log on the Windows 10 client contains an Event ID 20221 from the RasClient source that includes the following error message.

“The user [username] dialed a connection named [connection] which has failed. The error code returned on failure is 0.”

Always On VPN and Azure MFA ESTS Token Error

NPS Event Log

Reviewing the event logs on the NPS server reveals more information. The Security event log contains an Event ID 6274 from the Microsoft Windows security auditing source that includes the following error message.

“Network Policy Server discarded the request for a user. Contact the Network Policy Administrator for more information.”

Always On VPN and Azure MFA ESTS Token Error

ESTS Token Error

Digging deeper in the operational event log on the NPS server, the AuthZAdminCh log (Applications and Services Logs > Microsoft > AzureMfa > AuthZ) contains an Event ID 3 from the AuthZ source indicating an ESTS_TOKEN_ERROR message.

Always On VPN and Azure MFA ESTS Token Error

Troubleshooting ESTS Token Error

Follow the steps below to troubleshoot the ESTS_TOKEN_ERROR.

Prerequisites

Ensure that all prerequisites are met. Validate the user is being synced to Azure Active Directory and that it is properly licensed for Azure MFA.

Certificates

As part of the NPS extension configuration, a certificate is created on the NPS server that is uploaded to Azure Active Directory. To validate the certificate was created and uploaded correctly, follow the troubleshooting guidance found here.

Enterprise Applications

The Azure Multi-Factor Auth Client and the Azure Multi-Factor Auth Connector enterprise applications must be enabled to support the NPS extension for Azure MFA. To confirm they are enabled, open an elevated PowerShell command window on the server where the Azure AD Connector is installed and run the following PowerShell commands.

Import-Module MSOnline
Connect-MsolService

Get-MsolServicePrincipal -AppPrincipalId “981f26a1-7f43-403b-a875-f8b09b8cd720” | Select-Object DisplayName, AccountEnabled

Get-MsolServicePrincipal -AppPrincipalId “1f5530b3-261a-47a9-b357-ded261e17918” | Select-Object DisplayName, AccountEnabled

Always On VPN and Azure MFA ESTS Token Error

If either or both enterprise applications are not enabled, enable them using the following PowerShell commands.

Set-MsolServicePrincipal -AppPrincipalId “981f26a1-7f43-403b-a875-f8b09b8cd720” -AccountEnabled $True

Set-MsolServicePrincipal -AppPrincipalId “1f5530b3-261a-47a9-b357-ded261e17918” -AccountEnabled $True

Once complete, restart the IAS service on the NPS server using the following PowerShell command.

Restart-Service IAS -PassThru

Additional Information

Windows 10 Always On VPN Network Policy Server (NPS) Load Balancing Strategies

Deploy Windows 10 Always On VPN with Microsoft Intune

Windows 10 Always On VPN Hands-On Training Classes Now Available

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