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 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

Always On VPN SSTP Load Balancing with Citrix NetScaler ADC

Always On VPN SSTP Load Balancing with Citrix NetScaler ADCOne of the many advantages of using Windows Server Routing and Remote Access Service (RRAS) as the VPN server to support Windows 10 Always On VPN connections is that it includes support for the Secure Socket Tunneling Protocol (SSTP). SSTP is a TLS-based VPN protocol that is easy to configure and deploy and is very firewall friendly. This ensures consistent and reliable connectivity even behind restrictive firewalls. The Citrix ADC (formerly NetScaler) is a popular platform for load balancing Always On VPN connections. In this article I’ll describe how to configure load balancing on the Citrix ADC for RRAS VPN connections using the SSTP VPN protocol.

Special Note: In December 2019 a serious security vulnerability was discovered on the Citrix ADC that gives an unauthenticated attacker the ability to arbitrarily execute code on the appliance. As of this writing a fix is not available (due end of January 2020) but a temporary workaround can be found here.

Load Balancing SSTP

Previously I’ve written about some of the use cases and benefits of SSTP load balancing as well as the options for offloading TLS for SSTP VPN connections. Load balancing SSTP eliminates single points of failure and enables support for multiple RRAS VPN servers to increase scalability. It is generally recommended that the Citrix ADC be configured to pass through encrypted SSTP VPN connections. However, TLS offloading can be configured to improve performance and reduce resource utilization on VPN servers, if required.

Configuration

Load balancing SSTP on the Citrix ADC is straightforward and not unlike load balancing a common HTTPS web server. Below are specific settings and parameters required to load balance SSTP using the Citrix ADC.

Note: This article is not a comprehensive configuration guide for the Citrix ADC. It assumes the administrator is familiar with basic load balancing concepts and has experience configuring the Citrix ADC.

Service Settings

The load balancing service for SSTP VPN should be configured to use TCP port 443 and the SSL_BRIDGE protocol. If TLS offload is required, TCP port 80 and the HTTP protocol can be configured. Additional configuration is required on the RRAS server when TLS offload is enabled, however. Detailed information for configuring RRAS and SSTP for TLS offload can be found here.

Always On VPN SSTP Load Balancing with Citrix NetScaler ADC

Virtual Server Settings

The virtual server is configured to use TCP port 443. It is recommended to use SSLSESSION persistence.

Always On VPN SSTP Load Balancing with Citrix NetScaler ADC

The LEASTCONNECTION load balancing method is the recommend option for load balancing method.

Always On VPN SSTP Load Balancing with Citrix NetScaler ADC

Service Monitoring

Using the default TCP monitor (tcp-default) is not recommended for monitoring SSTP, as a simple TCP port check does not accurately reflect the health of the SSTP service running on the RRAS server. To more precisely monitor the SSTP service status, a new custom monitor must be created and bound to the load balancing services. Follow the steps below to configure a custom SSTP VPN monitor on the Citrix ADC.

  1. Open the Citrix ADC management console and expand Traffic Management.
  2. Select Monitors.
  3. Click Add.
  4. Enter a descriptive name in the Name field.
  5. Select HTTP form the Type drop-down list and click Select.
  6. Adjust the Interval and Response Time-out values according to your requirements.
  7. Enter 401 in the Response Codes field and click the “+” button.
  8. In the Response Codes field click the “x” next to 200.
  9. In the HTTP Request field enter HEAD /sra_{BA195980-CD49-458b-9E23-C84EE0ADCD75}/.
  10. Check the box next to Secure (not required if TLS offload is enabled).
  11. Select ns_default_ssl_profile_backend from the SSL profile drop-down list (not required if TLS offload is enabled).
  12. Click Create.

Always On VPN SSTP Load Balancing with Citrix NetScaler ADC

Once complete, bind the new service monitor to the load balancing services or service groups accordingly.

TLS Offload

It is generally recommended that TLS offload not be enabled for SSTP VPN. However, if TLS offload is desired, it is configured in much the same way as a common HTTPS web server. Specific guidance for enabling TLS offload on the Citrix ADC can be found here. Details for configuring RRAS and SSTP to support TLS offload can be found here.

Certificates

When enabling TLS offload for SSTP VPN connections it is recommended that the public SSL certificate be installed on the RRAS server, even though TLS processing will be handled on the Citrix ADC and HTTP will be used between the Citrix ADC and the RRAS server. If installing the public SSL certificate on the RRAS server is not an option, additional configuration will be required. Specifically, TLS offload for SSTP must be configured using the Enable-SSTPOffload.ps1 PowerShell script, which can be found here.

Once the script has been downloaded, open an elevated PowerShell command window and enter the following command.

.\Enable-SSTPOffload.ps1 -CertificateHash [SHA256 Certificate Hash of Public SSL Certificate] -Restart

Example:

.\Enable-SSTPOffload.ps1 -CertificateHash ‘C3AB8FF13720E8AD9047DD39466B3C8974E592C2FA383D4A3960714CAEF0C4F2’ -Restart

Re-Encryption

When offloading TLS for SSTP VPN connections, all traffic between the Citrix ADC and the RRAS server will be sent in the clear using HTTP. In some instances, TLS offload is required only for traffic inspection, not performance gain. In this scenario the Citrix ADC will be configured to terminate and then re-encrypt connections to the RRAS server. When terminating TLS on the Citrix ADC and re-encrypting connections to the RRAS server is required, the same certificate must be used on both the Citrix ADC and the RRAS server. Using different certificates on the RRAS server and the load balancer is not supported.

Additional Information

Windows 10 Always On VPN Load Balancing and SSL Offload

SSL Offload Configuration for Citrix ADC (NetScaler)

Windows 10 Always On VPN SSTP Load Balancing with Kemp LoadMaster

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

Windows 10 Always On VPN Connects then Disconnects

Windows 10 Always On VPN SSL Certificate Requirements for SSTP

Always On VPN Device Tunnel with Azure VPN Gateway

Always On VPN Device Tunnel with Azure VPN GatewayAlways On VPN is infrastructure independent, which allows for many different deployment scenarios including on-premises and cloud-based. In Microsoft Azure, the Azure VPN gateway can be configured to support Windows 10 Always On VPN client connections in some scenarios. Recently I wrote about using the Azure VPN gateway for Always On VPN user tunnels. In this post I’ll describe how to configure the Azure VPN gateway to support an Always On VPN device tunnel.

Limitations

There are a few crucial limitations that come with using the Azure VPN gateway for Always On VPN. Importantly, the Azure VPN gateway can support either user tunnels or device tunnels, not both at the same time. In addition, Azure supports only a single VPN gateway per VNet, so deploying an additional VPN gateway in the same VNet to support Always On VPN user tunnels is not an option.

Root CA Certificate

The Always On VPN device tunnel is authenticated using a machine certificate issued to domain-joined Windows 10 Enterprise edition clients by the organization’s internal Certification Authority (CA). The CA’s root certificate must be uploaded to Azure for the VPN gateway to authorize device tunnel connections. The root CA certificate can be exported using the Certification Authority management console (certsrv.msc) or via the command line.

Export Certificate – GUI

Follow the steps below to export a root CA certificate using the Certification Authority management console.

1. On the root CA server, open the Certification Authority management console.
2. Right-click the CA and choose Properties.
3. Select the CA server’s certificate and choose View Certificate.
4. Select the Details tab and click Copy to File.
5. Click Next.
6. Choose Base-64 encoded X.509 (.CER).

Always On VPN Device Tunnel with Azure VPN Gateway

7. Click Next.
8. Enter a location to save the file to.
9. Click Next, Finish, and Ok.

Export Certificate – Command Line

Follow the steps below to export a root CA certificate using the command line.

1. On the root CA server, open an elevated command window (not a PowerShell window).
2. Enter certutil.exe -ca.cert root_certificate.cer.
3. Enter certutil.exe -encode root.cer root_certificate_base64.cer.

Copy Public Key

1. Open the saved root certificate file using Notepad.
2. Copy the file contents between the BEGIN CERTIFICATE and END CERTIFICATE tags, as shown here. Use caution and don’t copy the carriage return at the end of the string.

Always On VPN Device Tunnel with Azure VPN Gateway

Point-to-Site Configuration

The Azure VPN gateway must be deployed as a Route-Based gateway to support point-to-site VPN connections. Detailed requirements for the gateway can be found here. Once the VPN gateway has been provisioned, follow the steps below to enable point-to-site configuration for Always On VPN device tunnels.

1. In the navigation pane of the Azure VPN gateway settings click Point-to-site configuration.
2. Click the Configure now link and specify an IPv4 address pool to be assigned to VPN clients. This IP address pool must be unique in the organization and must not overlap with an IP address ranges defined in the Azure virtual network.
3. From the Tunnel type drop-down list select IKEv2.
4. In the Root certificates section enter a descriptive name for the certificate in the Name field.
5. Copy and paste the Base64 encoded public key copied previously into the Public certificate data field.
6. Click Save to save the configuration.

Always On VPN Device Tunnel with Azure VPN Gateway

VPN Client Configuration

To support the Always On VPN device tunnel, the client must have a certificate issued by the internal CA with the Client Authentication Enhanced Key Usage (EKU). Detailed guidance for deploying a Windows 10 Always On VPN device tunnel can be found here.

Download VPN Configuration

1. Click Point-to-site configuration.
2. Click Download VPN client.
3. Click Save.
4. Open the downloaded zip file and extract the VpnSettings.xml file from the Generic folder.
5. Copy the FQDN in the VpnServer element in VpnSettings.xml. This is the FQDN that will be used in the template VPN connection and later in ProfileXML.

Create a Test VPN Connection

It is recommended to create a test VPN connection to perform validation testing of the Azure VPN gateway before provisioning an Always On VPN device tunnel broadly. On a domain-joined Windows 10 enterprise client, create a new VPN connection using IKEv2 with machine certificate authentication. Use the VPN server FQDN copied from the VpnSettings.xml file previously.

Always On VPN Device Tunnel with Azure VPN Gateway

Create an Always On VPN Connection

Once the VPN has been validated using the test profile created previously, an Always On VPN profile can be created and deployed using Intune, SCCM, or PowerShell. The following articles can be used for reference.

Deploy Always On VPN device tunnel using PowerShell

Deploy Always On VPN device tunnel using Intune

IKEv2 Security Configuration

The default IKEv2 security parameters used by the Azure VPN gateway are better than Windows Server, but the administrator will notice that a weak Diffie-Hellman (DH) key (Group 2 – 1024 bit) is used during IPsec phase 1 negotiation.

Always On VPN Device Tunnel with Azure VPN Gateway

Use the following PowerShell commands to update the default IKEv2 security parameters to recommended baseline defaults, including 2048-bit keys (DH group 14) and AES-128 for improved performance.

Connect-AzAccount
Select-AzSubscription -SubscriptionName [Azure Subscription Name]

$Gateway = [Gateway Name]
$ResourceGroup = [Resource Group Name]

$IPsecPolicy = New-AzVpnClientIpsecParameter -IpsecEncryption AES128 -IpsecIntegrity SHA256 -SALifeTime 28800 -SADataSize 102400000 -IkeEncryption AES128 -IkeIntegrity SHA256 -DhGroup DHGroup14 -PfsGroup PFS14

Set-AzVpnClientIpsecParameter -VirtualNetworkGatewayName $Gateway -ResourceGroupName $ResourceGroup -VpnClientIPsecParameter $IPsecPolicy

Note: Be sure to update the cryptography settings on the test VPN connection and in ProfileXML for Always On VPN connections to match the new VPN gateway settings. Failing to do so will result in an IPsec policy mismatch error.

Additional Information

Windows 10 Always On VPN User Tunnel with Azure VPN Gateway

Windows 10 Always On VPN IKEv2 Security Configuration

Windows 10 Always On VPN Device Tunnel Configuration using Microsoft Intune

Windows 10 Always On VPN Device Tunnel Configuration using PowerShell

Windows 10 Always On VPN Options for Azure Deployments

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 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 SSTP Load Balancing with F5 BIG-IP

Always On VPN SSTP Load Balancing with F5 BIG-IP The Windows Server Routing and Remote Access Service (RRAS) includes support for the Secure Sockets Tunneling Protocol (SSTP), which is a Microsoft proprietary VPN protocol that uses SSL/TLS for security and privacy of VPN connections. The advantage of using SSTP for Always On VPN is that it is firewall friendly and ensures consistent remote connectivity even behind highly restrictive firewalls.

Load Balancing SSTP

In a recent post, I described some of the use cases and benefits of SSTP load balancing as well as the offloading of TLS for SSTP VPN connections. Using a load balancer for SSTP VPN connections increases scalability, and offloading TLS for SSTP reduces resource utilization and improves performance for VPN connections. There are positive security benefits too.

Configuration

Enabling load balancing for SSTP on the F5 BIG-IP load balancer is fundamentally similar to load balancing HTTPS web servers. However, there are a few subtle but important differences.

Default Monitor

The default HTTP and HTTPS monitors on the F5 will not accurately reflect the health of the SSTP service running on the RRAS server. In addition, using a simple TCP port monitor could yield unexpected results. To ensure accurate service status monitoring, a new custom monitor must be created to validate the health of the SSTP service.

Custom SSTP Monitor

Open the F5 BIG-IP management console and follow the steps below to create and assign a new custom monitor for SSTP.

Create Monitor

1. In the navigation tree highlight Local Traffic.
2. Click Monitors.
3. Click Create.

Always On VPN SSTP Load Balancing with F5 BIG-IP

4. Enter a descriptive name in the Name field and from the Type drop-down list choose HTTP if TLS offload is enabled, or HTTPS if it is not.
5. In the Send String field enter HEAD /sra_{BA195980-CD49-458b-9E23-C84EE0ADCD75}/ HTTP/1.1\r\nHost:r\nConnection: Close\r\n\r\n.
6. In the Receive String field enter HTTP/1.1 401.
7. Click Finished.

Always On VPN SSTP Load Balancing with F5 BIG-IP

Assign Monitor

1. Below Local Traffic click Pools.
2. Click on the SSTP VPN server pool.
3. In the Health Monitors section select the SSTP VPN health monitor from the Available list and make it Active.
4. Click Update.

Always On VPN SSTP Load Balancing with F5 BIG-IP

CLI Configuration

If you prefer to configure the SSTP VPN monitor using the F5’s Command Line Interface (CLI), you can download the monitor configuration from my GitHub here.

TLS Offload

It is generally recommended that TLS offload not be enabled for SSTP VPN. However, if TLS offload is desired, it is configured in much the same way as a common HTTPS web server. Specific guidance for enabling TLS offload on the F5 BIG-IP can be found here. Details for configuring RRAS and SSTP to support TLS offload can be found here.

Certificates

When enabling TLS offload for SSTP VPN connections it is recommended that the public SSL certificate be installed on the RRAS server, even though TLS processing will be handled on the F5 and HTTP will be used between the F5 and the RRAS server. If installing the public SSL certificate on the RRAS server is not an option, additional configuration will be required. Specifically, TLS offload for SSTP must be configured using the Enable-SSTPOffload PowerShell script, which can be found here.

Once the script has been downloaded, open an elevated PowerShell command window and enter the following command.

Enable-SSTPOffload -CertificateHash [SHA256 Certificate Hash of Public SSL Certificate] -Restart

Example:

Enable-SSTPOffload -CertificateHash “C3AB8FF13720E8AD9047DD39466B3C8974E592C2FA383D4A3960714CAEF0C4F2” -Restart

Re-Encryption

When offloading TLS for SSTP VPN connections, all traffic between the F5 and the RRAS server will be sent in the clear using HTTP. In some instances, TLS offload is required only for traffic inspection, not performance gain. In this scenario the F5 will be configured to terminate and then re-encrypt connections to the RRAS server. When terminating TLS on the F5 and re-encrypting connections to the RRAS server is required, the same certificate must be used on both the F5 and the RRAS server. Using different certificates on the RRAS server and the load balancer is not supported.

Additional Information

Windows 10 Always On VPN SSTP Load Balancing and SSL Offload

Windows 10 Always On VPN SSL Certificate Requirements for SSTP

Windows 10 Always On VPN ECDSA SSL Certificate Request for SSTP

Windows 10 Always On VPN SSTP Connects then Disconnects

Windows 10 Always On VPN Load Balancing Deployment Guide for Kemp Load Balancers

 

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

 

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