Always On VPN and Autopilot Hybrid Azure AD Join

Always On VPN and Autopilot Hybrid Azure AD Join

Windows Autopilot is a cloud-based technology that administrators can use to configure new devices wherever they may be, whether on-premises or in the field. Devices provisioned with Autopilot are Azure AD joined by default and managed using Microsoft Endpoint Manager. Optionally, an administrator can enable hybrid Azure AD join by also joining the device to an on-premises Active Directory domain using a domain join configuration profile in conjunction with the offline domain-join connector. Although enabling hybrid Azure AD join might sound appealing, there are specific deployment scenarios that present some rather unique and challenging problems when using this option.

Offline Hybrid Azure AD Join

For field-based devices, the device must have connectivity to a domain controller to support the initial login when the user has no local cached credentials. The Always On VPN device tunnel can be deployed in this scenario to provide connectivity and allow the user to log in to a new device the first time without being on-premises. The Always On VPN device tunnel is easily deployed using a Microsoft Endpoint Manager configuration profile. Certificates required to support the device tunnel can be deployed with Microsoft Endpoint Manager and one of the certificate connectors for Microsoft Endpoint Manager.

Windows 10 Professional

If a Windows 10 Professional device is configured using Autopilot, and hybrid Azure AD joined is enabled, the Always On VPN device tunnel can still be provisioned, but it won’t start automatically because it requires Enterprise Edition to be fully functional. This prevents the user from being able to logon the first time. The device must be upgraded to Enterprise Edition before the first user logon. There are multiple ways to accomplish this depending on the deployment scenario and activation requirements.

Multiple Activation Key

The easiest way to upgrade Windows 10 Professional to Enterprise Edition is to obtain a Multiple Activation Key (MAK) and deploy that to clients using a Microsoft Endpoint Manager configuration profile. Follow the steps below to create a configuration profile to perform this upgrade.

  1. Open the Microsoft Endpoint Manager console and click on Devices > Configuration Profiles.
  2. Click Create profile.
  3. Select Windows 10 and later in the Platform drop-down list.
  4. Select Templates in the Profile type drop-down list.
  5. Select Edition upgrade and mode switch from the list of templates.
  6. Click Create.

Use the following steps to configure the settings for the configuration profile.

  1. Enter a descriptive name for the configuration profile in the Name field.
  2. Enter a description for the profile in the Description field (optional).
  3. Click Next.
  4. Expand the Edition Upgrade section and select Windows 10 Enterprise from the Edition to upgrade to drop-down list.
  5. Enter your multiple activation product key in the Product Key field.

    Always On VPN and Autopilot Hybrid Azure AD Join

Once complete, assign the configuration profile to the appropriate groups and click Create.

KMS Activation

If Key Management Service (KMS) activation is required, follow the steps listed previously for MAK. Enter the KMS client setup key for Windows 10 Enterprise which is NPPR9-FWDCX-D2C8J-H872K-2YT43. The device will complete KMS activation when it can connect to the on-premises KMS host.

Subscription Activation

Windows 10 Enterprise Edition licensing is included in some Microsoft 365 subscriptions. This poses a unique challenge for hybrid Azure AD join scenarios, however. Specifically, subscription activation is a “step-up” process that requires Windows 10 Professional to have been successfully activated previously. Also, this occurs after the user logs on, but the user cannot log on unless the device tunnel is active. Catch 22!

Workaround

A multi-step process is required to address the limitations imposed by subscription activation. To begin, the device must be upgraded to Enterprise Edition, so the device tunnel is available for the initial user logon. This is a temporary, one-time upgrade to Enterprise Edition solely for the purpose of getting the device tunnel to connect and allow the user to authenticate.

To begin, download this PowerShell script and follow the steps below to deploy it to Windows 10 devices using Microsoft Endpoint Manager.

  1. Open the Microsoft Endpoint Manager console and click on Devices > Scripts.
  2. Click Add and select Windows 10.
  3. Enter a descriptive name for the configuration profile in the Name field.
  4. Enter a description for the profile in the Description field (optional).
  5. Click Next.
  6. Enter the location of the PowerShell script in the Script location field.
  7. Click Next, then assign the script to the appropriate device group(s) and click Add.

The PowerShell script will automatically install the KMS client setup key for Windows 10 Enterprise Edition, then restart the network interfaces to ensure the device tunnel starts. This will immediately upgrade the client device to Windows 10 Enterprise Edition and allow the user to authenticate.

Subscription activation with a step-up upgrade to Enterprise Edition still requires that Windows 10 Professional be activated first. To accomplish this, the embedded Windows 10 Professional key must be re-installed on the client. To do this, download this PowerShell script and follow the same steps listed previously to deploy a PowerShell script with Microsoft Endpoint Manager. However, this script should be assigned to users, not devices.

Once this script is run on the client it will be downgraded (temporarily) to Windows 10 Professional edition. After activation is successful, subscription activation will once again upgrade the client to Windows 10 Enterprise Edition.

Considerations

As you can see, the process of getting a Windows 10 Professional edition client onboarded in a hybrid Azure AD joined scenario is somewhat complex. My advice is to avoid this scenario whenever possible. Access to on-premises resources with the Always On VPN user tunnel with full single sign-on support is still available for users on Windows 10 devices that are Azure AD joined only. Unless there is a specific requirement to manage client devices using on-premises Active Directory and group policy, consider choosing native Azure AD join with Autopilot and manage devices using Microsoft Endpoint Manager exclusively.

Special Thanks

I would like to extend a special thank you to everyone in the Microsoft Endpoint Manager community who provided valuable input and feedback for me on this topic, especially John Marcum, Michael Niehaus, and Sandy Zeng. Follow the #MEMCM hashtag on Twitter to keep up on all things Microsoft Endpoint Manager.

Additional Information

Overview of Windows Autopilot

Windows 10 Subscription Activation

Windows 10 Always On VPN Class-Based Default Route and Microsoft Endpoint Manager

Windows 10 Always On VPN Device Tunnel and Custom Cryptography in Microsoft Endpoint Manager

Always On VPN Continue Connecting Prompt

Using the Extensible Authentication Protocol (EAP) with client certificates is the recommended best practice for authentication for Windows 10 Always On VPN deployments. EAP, and especially Protected EAP (PEAP), has a lot of settings to configure and it is not uncommon to encounter issues related to some parameters being defined incorrectly. This post covers one of the more common issues related to EAP/PEAP misconfiguration.

Action Needed?

When establishing an Always On VPN user tunnel connection, users may find the connection does not complete automatically, and they are informed that additional action is needed.

Clicking on the VPN connection and then clicking Connect prompts the user with the following message.

“Action needed. Continue connecting? We don’t have enough info to validate the server. You can still connect if you trust this server.”

Common Causes

This message can occur when (EAP) is used and is configured to perform server validation with a restricted set of NPS servers, as shown here.

NPS Server Certificate

The NPS server performing authentication for the connection request must have a certificate that includes a subject name that matches one of the names of the NPS servers defined in the EAP configuration. The certificate must be issued by the organizations private certification authority (CA).

EAP Configuration

Alternatively, the client-side EAP configuration may be incorrect. Although the NPS server may have the correct hostname configured on its certificate, it may not be entered correctly on the client. Ensure the hostname listed in the “Connect to these servers” field matches the subject name or SAN of the NPS server certificate defined in the network policy used for the Always On VPN user tunnel. Look carefully at the syntax when defining multiple NPS servers. Multiple servers are separated by a semi-colon and there are no additional spaces. Missing either one of these critical details will result in connection prompts. Also, ensure that all NPS servers used for authentication (those defined on the VPN server) are included in this list.

Note: Administrators must ensure that all VPN clients have updated their EAP configuration before adding additional NPS servers to the environment. Failure to do so will result in connection prompts.

Security Best Practice

To be clear, the behavior above is not ideal from a security perspective. Validating the NPS server before authenticating is crucial to ensuring the highest level of security and assurance, preventing credential theft from a man-in-the-middle attack. For this reason, it is recommended that users not be given the choice to authorize an NPS server. Authorized NPS servers should be defined by administrators exclusively. This is accomplished by selecting the option “Don’t ask user to authorize new servers or trusted CAs” in the Notifications before connecting drop-down list, and by selecting the option “Don’t prompt user to authorize new servers or trusted certification authorities“.

Additional Information

Always On VPN Network Policy Server (NPS) Load Balancing

Always On VPN and Windows Server 2019 NPS Bug

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 Device Tunnel Only Deployment Considerations

Always On VPN Device Tunnel Only Deployment ConsiderationsRecently I wrote about Windows 10 Always On VPN device tunnel operation and best practices, explaining its common uses cases and requirements, as well as sharing some detailed information about authentication, deployment recommendations, and best practices. I’m commonly asked if deploying Always On VPN using the device tunnel exclusively, as opposed to using it to supplement the user tunnel, is supported or recommended. I’ll address those topics in detail here.

Device Tunnel Only?

To start, yes, it is possible to deploy Windows 10 Always On VPN using only the device tunnel. In this scenario the administrator will configure full access to the network instead of limited access to domain infrastructure services and management servers.

Is It Recommended?

Generally, no. Remember, the device tunnel was designed with a specific purpose in mind, that being to provide pre-logon network connectivity to support scenarios such as logging on without cached credentials. Typically, the device tunnel is best used for its intended purpose, which is providing supplemental functionality to the user tunnel.

Deployment Considerations

The choice to implement Always On VPN using only the device tunnel is an interesting one. There are some potential advantages to this deployment model, but it is not without some serious limitations. Below I’ve listed some of the advantages and disadvantages to deploying the device tunnel alone for Windows 10 Always On VPN.

Advantages

Using the device tunnel alone does have some compelling advantages over the standard two tunnel (device tunnel/user tunnel) deployment model. Consider the following.

  • Single VPN Connection – Deploying the device tunnel alone means a single VPN connection to configure, deploy, and manage on the client. This also results in less concurrent connections and, importantly, less IP addresses to allocate and provision.
  • Reduced Infrastructure – The device tunnel is authenticated using only the device certificate. This certificate check is performed directly on the Windows Server Routing and Remote Access Service (RRAS) VPN server, eliminating the requirement to deploy Network Policy Server (NPS) servers for authentication.
  • User Transparency – The device tunnel does not appear in the modern Windows UI. The user will not see this connection if they click on the network icon in the notification area. In addition, they will not see the device tunnel connection in the settings app under Network & Internet > VPN. This prevents casual users from playing with the connection settings, and potentially deleting the connection entirely. It’s not that they can’t delete the device tunnel however, it’s just not as obvious.
  • Simplified Deployment – Deploying the device tunnel is less complicated than deploying the user tunnel. The device tunnel is provisioned once to the device and available to all users. This eliminates the complexity of having to deploy the user tunnel in each individual user’s profile.

Disadvantages

While there are some advantages to using the device tunnel by itself, this configuration is not without some serious limitations. Consider the following.

  • IKEv2 Only – The device tunnel uses the IKEv2 VPN protocol exclusively. It does not support SSTP. While IKEv2 is an excellent protocol in terms of security, it is commonly blocked by firewalls. This will prevent some users from accessing the network remotely depending on their location.
  • Limited OS Support – The device tunnel is only supported on Windows 10 Enterprise edition clients, and those clients must be joined to a domain. Arguably the device tunnel wouldn’t be necessary if the client isn’t domain joined, but some organizations have widely deployed Windows 10 Professional, which would then preclude them from being able to use the device tunnel.
  • Machine Certificate Authentication Only – The device tunnel is authenticated using only the certificate issued to the device. This means anyone who logs on to the device will have full access to the internal network. This may or may not be desirable, depending on individual requirements.
  • No Mutual Authentication – When the device tunnel is authenticated, the server performs authentication of the client, but the client does not authenticate the server. The lack of mutual authentication increases the risk of a man-in-the-middle attack.
  • CRL Checks Not Enforced – By default, RRAS does not perform certificate revocation checking for device tunnel connections. This means simply revoking a certificate won’t prevent the device from connecting. You’ll have to import the client’s device certificate into the Untrusted Certificates certificate store on each VPN server. Fortunately, there is a fix available to address this limitation, but it involves some additional configuration. See Always On VPN Device Tunnel and Certificate Revocation for more details.
  • No Support for Azure Conditional Access – Azure Conditional Access requires EAP authentication. However, the device tunnel does not use EAP but instead uses a simple device certificate check to authenticate the device.
  • No Support for Multifactor Authentication – As the device tunnel is authenticated by the RRAS VPN server directly and authentication requests are not sent to the NPS server, it is not possible to integrate MFA with the device tunnel.
  • Limited Connection Visibility – Since the device tunnel is designed for the device and not the user it does not appear in the list of active network connections in the Windows UI. There is no user-friendly connection status indicator, although the connection can be viewed using the classic network control panel applet (ncpa.cpl).

Summary

The choice to deploy Windows 10 Always On VPN using the device tunnel alone, or in conjunction with the user tunnel, is a design choice that administrators must make based on their individual requirements. Using the device tunnel alone is supported and works but has some serious drawbacks and limitations. The best experience will be found using the device tunnel as it was intended, as an optional component to provide pre-logon connectivity for an existing Always On VPN user tunnel.

Additional Information

Windows 10 Always On VPN Device Tunnel with Azure VPN Gateway

Windows 10 Always On VPN Device Tunnel and Certificate Revocation

Windows 10 Always On VPN Device Tunnel Configuration with Microsoft Intune

Windows 10 Always On VPN Device Tunnel Does Not Connect Automatically

Windows 10 Always On VPN Device Tunnel Missing in Windows 10 UI

Deleting a Windows 10 Always On VPN Device Tunnel

Windows 10 Always On VPN Device Tunnel Configuration using PowerShell

Windows 10 Always On VPN IKEv2 Features and Limitations

Always On VPN Error Code 858

Always On VPN Error Code 858When configuring Windows 10 Always On VPN using Extensible Authentication Protocol (EAP), the administrator may encounter a scenario in which the client connection fails. The event log will include an event ID 20227 from the RasClient source that includes the following error message.

“The user [domain\username] dialed a connection named [connection name] which has failed. The error code returned on failure is 858.”

Always On VPN Error Code 858

RasClient Error 858

RasClient error code 858 translates to ERROR_EAP_SERVER_CERT_EXPIRED. Intuitively, this indicates that the Server Authentication certificate installed on the Network Policy Server (NPS) has expired. To resolve this issue, renew the certificate on the NPS server.

Additional Information

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

Windows 10 Always On VPN and Windows Server 2019 NPS Bug

Windows 10 Always On VPN Error Code 864

Microsoft Intune NDES Connector Error 0x80004003

Microsoft Intune NDES Connector Error 0x80004003To support certificate deployment for non-domain Windows 10 Always On VPN clients, a Windows Server with the Network Device Enrollment Service (NDES) role can be provisioned on-premises. In addition, the Microsoft Intune Connector must be installed and configured on the NDES server to allow Intune-managed clients to request and receive certificates from the on-premises Certification Authority (CA) server.

Connection Status Error

After installing the Microsoft Intune Connector, the administrator may encounter the following error message.

“An error occurred while connecting to the Intune Service. Error code is 0x80004003. The NDES Connector will retry the connection as soon as possible.”

 Microsoft Intune NDES Connector Error 0x80004003

IE Enhanced Security Configuration

This error can occur if Internet Explorer Enhanced Security Configuration (ESC) is enabled. To resolve this issue, disable ESC for administrators and users by opening the Server Manager on the NDES server and performing the following steps.

1. In the navigation pane click Local Server.
2. Click the On link next to IE Enhanced Security Configuration.
3. Click Off in the Administrators section.
4. Click Off in the Users section
5. Click Ok.

Microsoft Intune NDES Connector Error 0x80004003

Once complete, restart the NDES Connector service using the following PowerShell command.

Restart-Service NDESConnectorSvc -PassThru

Additional Configuration

Microsoft Intune NDES Connector Setup Wizard Ended Prematurely

Microsoft Intune NDES Connector Setup Wizard Ended Prematurely

Microsoft Intune NDES Connector Setup Wizard Ended PrematurelyA Windows Server with the Network Device Enrollment Service (NDES) role can be provisioned on-premises to support certificate deployment for non-domain Windows 10 Always On VPN clients. In addition, the Microsoft Intune Connector must be installed and configured on the NDES server to allow Intune-managed clients to request and receive certificates from the on-premises Certification Authority (CA) server.

Setup Wizard Ended Prematurely

When installing the Microsoft Intune Connector, the administrator may encounter a scenario where the setup wizard fails with the following error message.

“Microsoft Intune Connector Setup Wizard ended prematurely because of an error. Your system has not been modified. To install this program at a later time, run Setup Wizard again. Click the Finish button to exit the Setup Wizard.”

Microsoft Intune NDES Connector Setup Wizard Ended Prematurely

Cryptographic Service Provider

This error can occur if the NDES server certificate template is configured to use the Key Storage Provider cryptography service provider (CSP). When configuring the certificate template for the NDES server, the Legacy Cryptography Service Provider must be used, as shown here.

Microsoft Intune NDES Connector Setup Wizard Ended Prematurely

Additional Information

Deploying Windows 10 Always On VPN with Intune using Custom ProfileXML

Windows 10 Always On VPN Device Tunnel Configuration using Microsoft Intune

Deploying Windows 10 Always On VPN with Microsoft Intune

 

Always On VPN Device Tunnel and Certificate Revocation

Always On VPN Device Tunnel and Certificate RevocationRecently I wrote about denying access to Windows 10 Always On VPN users or computers. In that post I provided specific guidance for denying access to computers configured with the device tunnel. To summarize, the process involved exporting the device certificate from the issuing Certification Authority (CA) server and placing it in the Untrusted Certificates certificate store on each VPN server. In theory, simply revoking the device certificate should be all that’s required to prevent device tunnel connections.

Revocation Check Failure

As it turns out, a bug in Windows Server Routing and Remote Access prevents this from working as expected. Windows Server 2012 R2, 2016, and 2019 all fail to check the Certificate Revocation List (CRL) for IKEv2 VPN connections using machine certificate authentication (for example an Always On VPN device tunnel).

Updates for Windows Server

Microsoft has released fixes to support device tunnel certificate revocation for the following operating systems.

Windows Server 2019 – KB4505658 (build 17763.652)

Windows Server 2016 – KB4503294 (build 14393.3053)

Windows Server 2012/R2 – Will not be updated.

Enable Revocation Check

Additional configuration is required to enable support for CRL checking. Microsoft published guidance for configuring CRL revocation checks for IKEv2 VPN connections using machine certificate authentication here. Specifically, administrators must enable the RootCertificateNameToAccept parameter and set a registry key to enable this functionality.

Open an elevated PowerShell window and run the following commands to enable CRL checking for IKEv2 VPN connections using machine certificate authentication.

$Thumbprint = ‘Root CA Certificate Thumbprint’
$RootCACert = (Get-ChildItem -Path cert:\LocalMachine\root | Where-Object {$_.Thumbprint -eq $Thumbprint})
Set-VpnAuthProtocol -RootCertificateNameToAccept $RootCACert -PassThru

New-ItemProperty -Path ‘HKLM:\SYSTEM\CurrentControlSet\Services\RemoteAccess\Parameters\Ikev2\’ -Name CertAuthFlags -PropertyTYpe DWORD -Value ‘4’ -Force

Restart-Service RemoteAccess -PassThru

Always On VPN Device Tunnel and Certificate Revocation

A PowerShell script to update the RootCertificateNameToAccept parameter on multiple VPN servers can be found here.

Revoking Certificates

To prevent a Windows 10 Always On VPN device tunnel connection, the administrator must first revoke the certificate on the issuing CA. Next, open an elevated command window an enter the following commands. Repeat these steps on each VPN server in the enterprise.

certutil -urlcache * delete
certutil -setreg chain\ChainCacheResyncFiletime @now

Additional Information

Denying Access to Windows 10 Always On VPN Users or Computers

Blocking VPN Clients that use Revoked Certificates

PowerShell Script to Configure RootCertificateNameToAccept on GitHub

 

 

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), Client Authentication (1.3.6.1.5.5.7.3.2), KDC Authentication (1.3.6.1.5.2.3.5), and Smart Card Logon (1.3.6.1.4.1.311.20.2.2) Enhanced Key Usage (EKU). Administrators can duplicate the Kerberos Authentication template for this purpose.

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

 

%d bloggers like this: