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

Renew DirectAccess Self-Signed Certificates

Renew DirectAccess Self-Signed CertificatesWhen DirectAccess is deployed using the Getting Started Wizard (GSW), sometimes referred to as the “simplified deployment” method, self-signed certificates are created during the installation and used for the IP-HTTPS IPv6 transition technology, the Network Location Server (NLS), and for RADIUS secret encryption.

Renew DirectAccess Self-Signed Certificates

Certificate Expiration

These self-signed certificates expire 5 years after they are created, which means many DirectAccess administrators who have used this deployment option will need to renew these certificates at some point in the future. Unfortunately, there’s no published guidance from Microsoft on how to accomplish this. However, the process is simple enough using PowerShell and the New-SelfSignedCertificate cmdlet.

PowerShell Script

Open an elevated PowerShell command window and run the following commands to renew the DirectAccess self-signed certificates.

# // Clone and install IP-HTTPS certificate

$iphttpscert = (Get-ChildItem -Path Cert:\LocalMachine\My\ | Where-Object Thumbprint -eq ((Get-RemoteAccess).SslCertificate | Select-Object -ExpandProperty Thumbprint))
$newcert = New-SelfSignedCertificate -CloneCert $iphttpscert -FriendlyName “DirectAccess-IPHTTPS” | Select-Object -ExpandProperty Thumbprint
$cert = (Get-ChildItem -Path Cert:\LocalMachine\My\ | Where-Object Thumbprint -eq $newcert)
Set-RemoteAccess -SslCertificate $cert -PassThru

# // Clone and install NLS certificate

$nlscert = (Get-ChildItem -Path Cert:\LocalMachine\My\ | Where-Object Thumbprint -eq ((Get-RemoteAccess).NlsCertificate | Select-Object -ExpandProperty Thumbprint))
$newcert = New-SelfSignedCertificate -CloneCert $nlscert -FriendlyName “DirectAccess-NLS” | Select-Object -ExpandProperty Thumbprint
$cert = (Get-ChildItem -Path Cert:\LocalMachine\My\ | Where-Object Thumbprint -eq $newcert)
Set-DANetworkLocationServer -NLSOnDAServer -Certificate $cert

# // Clone RADIUS encryption certificate

$cert = (Get-ChildItem -Path Cert:\LocalMachine\My\ | Where-Object Subject -like “*radius-encrypt*”)
New-SelfSignedCertificate -CloneCert $cert -FriendlyName “Certificate issued by Remote Access for RADIUS shared secrets”

Script on GitHub

I’ve also published this script on GitHub. You can download Renew-DaSelfSignedCertificates.ps1 here.

Important Considerations

When the IP-HTTPS and NLS scripts above are executed, DirectAccess clients outside will be immediately disconnected and will be unable to reconnect until they update group policy (the RADIUS encryption certificate can be updated without impacting users). This will require connecting to the internal network locally or remotely using another VPN solution. In addition, internal clients that are not online when this change is made will be unable to access internal resources by name until they update group policy. If this happens, delete the Name Resolution Policy Table (NRPT) on the client using the following PowerShell command and reboot to restore connectivity.

Get-Item -Path “HKLM:\SOFTWARE\Policies\Microsoft\Windows NT\DNSClient\DnsPolicyConfig” | Remove-Item -Confirm:$false

Additional Information

PowerShell Recommended Reading for DirectAccess Administrators

Top 5 DirectAccess Troubleshooting PowerShell Commands

 

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

Denying Access to Always On VPN Users or Computers

Denying Access to Always On VPN Users or ComputersOnce Windows 10 Always On VPN has been deployed in production, it may be necessary at some point for administrators to deny access to individual users or computers. Commonly this occurs when an employee is terminated or leaves the company, or if a device is lost, stolen, or otherwise compromised. Typically, this means that user accounts and computer accounts in Active Directory are disabled, and any issued certificates are revoked. However, additional steps may be required to disconnect current VPN sessions or prevent future remote connections.

Certificate Revocation

When certificates are used for authentication, for example when a device tunnel is deployed, or a user tunnel is configured to use Extensible Authentication Protocol (EAP) with user certificate authentication, immediately revoking issued user and device certificates and publishing a new Certificate Revocation List (CRL) is recommended. However, this will not instantly prevent VPN access because revocation information is cached on the VPN and NPS servers, as well as any online responders. The process of flushing certificate revocation caches is challenging and time consuming as well.

Blocking Users

To immediately prevent users from accessing the VPN, a security group must be created in Active Directory that contains users that will be denied access. In addition, a Network Policy must be created on the Network Policy Server (NPS) that denies access to users belong to this security group.

NPS Configuration

Once the security group has been created, open the NPS management console (nps.msc) and perform the following steps.

  1. Expand Policies.
  2. Right-click Network Policies and choose New.
  3. Enter a descriptive name for the policy in the Policy name field.
  4. Select Remote Access Server (VPN-Dial up) from the Type of network access server drop-down list.
  5. Click Next.
  6. Click Add.
    1. Select User Groups.
    2. Click Add.
    3. Click Add Groups.
    4. Select the security group create for denied users.
    5. Click Ok twice.
  7. Click Next.
  8. Select Access denied.
  9. Click Next four times and click Finish.

Denying Access to Always On VPN Users or Computers

Denying Access to Always On VPN Users or Computers

Once complete, move the deny access policy so that it is before the policy that allows VPN access.

Denying Access to Always On VPN Users or Computers

Device Tunnel Considerations

Since device tunnel connections don’t use the NPS for authentication, blocking devices from establishing Always On VPN connections requires a different technique. Once again, revoking the computer certificate and publishing a new CRL is recommended, but isn’t immediately effective. To address this challenge, it is recommended that the computer certificate issued to the client be retrieved from the issuing CA and placed in the local computer’s Untrusted Certificates store on each VPN server, as shown here.

Note: The certificate must be imported on each VPN server in the organization.

Terminating Connections

Once the guidance above is put in to place, any user or device that is denied access will be unable to connect to the VPN. However, if a user or device is currently connected when these changes are implemented, additional steps must be taken to proactively terminate their existing session. When using Windows Server Routing and Remote Access Service (RRAS) as the VPN server, uUser sessions can be proactively terminated using RRAS management console or PowerShell.

GUI

To terminate an established Always On VPN connection, open the RRAS management console (rrasmgmt.msc), highlight Remote Access Clients, then right-click the client connection and choose Disconnect. Repeat the process for any additional connections established by the user or device.

Denying Access to Always On VPN Users or Computers

PowerShell

Alternatively, Always On VPN connections can also be terminated programmatically using PowerShell. To identify currently connected users on a VPN server, open an elevated PowerShell command window and run the following command.

Get-RemoteAccessConnectionStatistics | Format-Table -AutoSize

Next, to disconnect a user tunnel, identify the User Principal Name (UPN) of the user to disconnect and include it in the following PowerShell command.

Disconnect-VpnUser -UserName “user@corp.example.net”

To disconnect a device tunnel, identify the Fully-Qualified Domain Name (FQDN) of the device to disconnect and include it in the following PowerShell command.

Disconnect-VpnUser -UserName “client1.corp.example.net”

Additional Information

Windows 10 Always On VPN Hands-On Training

Always On VPN Updates to Improve Connection Reliability

Always On VPN Updates to Improve Connection ReliabilityA longstanding issue with Windows 10 Always On VPN is that of VPN tunnel connectivity reliability and device tunnel/user tunnel interoperability. Many administrators have reported that Always On VPN connections fail to establish automatically at times, that only one tunnel comes up at a time (user tunnel or device tunnel, but not both), or that VPN tunnels fail to establish when coming out of sleep or hibernate modes. Have a look at the comments on this post and you’ll get a good understanding of the issues with Always On VPN.

Recent Updates

The good news is that most of these issues have been resolved with recent updates to Windows 10 1803 and 1809. Specifically, the February 19, 2019 update for Windows 10 1803 (KB4487029) and the March 1, 2019 update for Windows 10 1809 (KB4482887) include fixes to address these known issues. Administrators are encouraged to deploy Windows 10 1803 with the latest updates applied when implementing Always On VPN. Windows 10 1809 with the latest updates applied is preferred though.

Persistent Issues

Although initial reports are favorable for these updates and based on my experience the effectiveness and reliability of Windows 10 Always On VPN is greatly improved, there have still been some reports of intermittent VPN tunnel establishment failures.

Possible Causes

During my testing, after applying the updates referenced earlier both device tunnel and user tunnel connections are established much more consistently than before the updates were applied. I did encounter some issues, however. Specifically, when coming out of sleep or hibernate, VPN connections would fail to establish. Occasionally VPN connections would fail after a complete restart.

NCSI

After further investigation it was determined that the connectivity failure was caused by the Network Connectivity Status Indicator (NCSI) probe failing, causing Windows to report “No Internet access”.

Always On VPN Updates to Improve Connection Reliability

Cisco Umbrella Roaming Client

In this instance the NCSI probe failure was caused by the Cisco Umbrella Roaming Client installed and running on the device. The Umbrella Roaming Client is security software that provides client protection by monitoring and filtering DNS queries. It operates by configuring a DNS listener on the loopback address. NCSI probes are known to fail when the DNS server is running on a different interface than is being tested.

Resolution

Microsoft released a fix for this issue in Windows 10 1709. The fix involves changing a group policy setting to disable interface binding when perform DNS lookups by the NCSI. You can enable this setting via Active Directory group policy by navigating to Computer Configuration > Administrative Templates > Network > Network Connectivity Status Indicator > Specify global DNS. Select Enabled and check the option to Use global DNS, as shown here.

Always On VPN Updates to Improve Connection Reliability

For testing purposes this setting can be enabled individual using the following PowerShell command.

New-ItemProperty -Path “HKLM:\SOFTWARE\Policies\Microsoft\Windows\NetworkConnectivityStatusIndicator\” -Name UseGlobalDNS -PropertyType DWORD -Value 1 -Force

Third-Party Software

As Always On VPN connectivity can be affected by NCSI, any third-party firewall or antivirus/antimalware solution could potentially introduce VPN connection instability. Observe NCSI operation closely when troubleshooting unreliable connections with Always On VPN.

Additional Information

Windows 10 1803 Update KB4487029

Windows 10 1809 Update KB4482887

Cisco Umbrella Roaming Client Limited Network Connectivity Warning

Network Connectivity Status Indicator (NCSI) Operation Explained

Always On VPN IKEv2 Features and Limitations

Always On VPN IKEv2 Features and LimitationsThe Internet Key Exchange version 2 (IKEv2) VPN protocol is a popular choice for Windows 10 Always On VPN deployments. IKEv2 is a standards-based IPsec VPN protocol with customizable security parameters that allows administrators to provide the highest level of protection for remote clients. In addition, it provides important interoperability with a variety of VPN devices, including Microsoft Windows Server Routing and Remote Access Service (RRAS) and non-Microsoft platforms such as Cisco, Checkpoint, Palo Alto, and others.

IKEv2 Limitations

IKEv2 is clearly the protocol of choice in terms of security. It supports modern cryptography and is highly resistant to interception. It’s not without some operational challenges, however. Consider the following.

Firewalls

IKEv2 uses UDP ports 500 and 4500 for communication. Unfortunately, these ports are not always open. Often, they are blocked by network administrators to prevent users from bypassing security controls or attackers from exfiltrating data.

Fragmentation

IKEv2 packets can become quite large at times, especially when using client certificate authentication with the Protected Extensible Authentication Protocol (PEAP). This can result in fragmentation occurring at the network layer. Unfortunately, many firewalls and network devices are configured to block IP fragments by default. This can result in failed connection attempts from some locations but not others.

Load Balancing

Load balancing IKEv2 connections is not entirely straightforward. Without special configuration, load balancers can cause intermittent connectivity issues for Always On VPN connections. Guidance for configuring IKEv2 load balancing on the Kemp LoadMaster and the F5 BIG-IP can be found here:

IKEv2 Fragmentation

IKEv2 fragmentation can be enabled to avoid IP fragmentation and restore reliable connectivity. IKEv2 fragmentation is supported in Windows 10 and Windows Server beginning with v1803. Guidance for enabling IKEv2 fragmentation on Windows Server RRAS can be found here. Support for IKEv2 fragmentation on non-Microsoft firewall/VPN devices is vendor-specific. Consult with your device manufacturer for more information.

IKEv2 Security and RRAS

Be advised that the default security settings for IKEv2 on Windows Server RRAS are very poor. The minimum recommended security settings and guidelines for implementing them can be found here.

IKEv2 or TLS?

IKEv2 is recommend for deployments where the highest level of security and protection is required for remote connections. In these scenarios, the sacrifice of ubiquitous availability in favor of ultimate security might be desired.

SSTP or another TLS-based VPN protocol is recommended if reliable operation and connectivity are desired. SSTP and TLS VPNs can be configured to provide very good security by following the security and implementation guidelines found here.

IKEv2 with TLS Fallback

In theory, preferring IKEv2 and falling back to the Secure Socket Tunneling Protocol (SSTP) or another TLS-based VPN protocol when IKEv2 is unavailable would seem like a logical choice. This would ensure the highest level of protection, while still providing reliable connectivity. Unfortunately, the Windows VPN client doesn’t work this way in practice. Details here.

Additional Information

Windows 10 Always On VPN IKEv2 Load Balancing with F5 BIG-IP

Windows 10 Always On VPN IKEv2 Load Balancing with Kemp LoadMaster

Windows 10 Always On VPN IKEv2 Fragmentation

Windows 10 Always On VPN IKEv2 and SSTP Fallback

Windows 10 Always On VPN IKEv2 Security Configuration

Windows 10 Always On VPN Certificate Requirements for IKEv2

Windows 10 Always On VPN Protocol Recommendations for Windows Server RRAS

Always On VPN IKEv2 Load Balancing with F5 BIG-IP

Always On VPN IKEv2 Load Balancing with F5 BIG-IPThe Internet Key Exchange version 2 (IKEv2) is the protocol of choice for Always On VPN deployments where the highest level of security is required. Implementing Always On VPN at scale often requires multiple VPN servers to provide sufficient capacity and to provide redundancy. Commonly an Application Delivery Controller (ADC) or load balancer is configured in front of the VPN servers to provide scalability and high availability for Always On VPN.

Load Balancing IKEv2

In a recent post I described some of the unique challenges load balancing IKEv2 poses, and I demonstrated how to configure the Kemp LoadMaster load balancer to properly load balance IKEv2 VPN connections. In this post I’ll outline how to configure IKEv2 VPN load balancing on the F5 BIG-IP load balancer.

Note: This article assumes the administrator is familiar with basic F5 BIG-IP load balancer configuration, such as creating nodes, pools, virtual servers, etc.

Initial Configuration

Follow the steps below to create a virtual server on the F5 BIG-IP to load balance IKEv2 VPN connections.

Pool Configuration

To begin, create two pools on the load balancer. The first pool will be configured to use UDP port 500, and the second pool will be configured to use UDP port 4500. Each pool is configured with the VPN servers defined as the individual nodes.

Always On VPN IKEv2 Load Balancing with F5 BIG-IP

Virtual Server Configuration

Next create two virtual servers, the first configured to use UDP port 500 and the second to use UDP port 4500.

Always On VPN IKEv2 Load Balancing with F5 BIG-IP

Persistence Profile

To ensure that both IKEv2 UDP 500 and 4500 packets are delivered to the same node, follow the steps below to create and assign a Persistence Profile.

1. Expand Local Traffic > Profiles and click Persistence.
2. Click Create.
3. Enter a descriptive name for the profile in the Name field.
4. Select Source Address Affinity from the Persistence Type drop-down list.
5. Click the Custom check box.
6. Select the option to Match Across Services.
7. Click Finished.

Always On VPN IKEv2 Load Balancing with F5 BIG-IP

Assign the new persistence profile to both UDP 500 and 4500 virtual servers. Navigate to the Resources tab on each virtual server and select the new persistence profile from the Default Persistence Profile drop-down list. Be sure to do this for both virtual servers.

Always On VPN IKEv2 Load Balancing with F5 BIG-IP

Additional Resources

Windows 10 Always On VPN IKEv2 Load Balancing with Kemp LoadMaster Load Balancer 

Windows 10 Always On VPN IKEv2 Security Configuration

Windows 10 Always On VPN and IKEv2 Fragmentation

Windows 10 Always On VPN Certificate Requirements for IKEv2

Video: Windows 10 Always On VPN Load Balancing with the Kemp LoadMaster Load Balancer

Always On VPN SSTP Connects then Disconnects

Always On VPN SSTP Connects then DisconnectsWhen Always On VPN clients are configured to use the Secure Socket Tunneling Protocol (SSTP) with Windows Server Routing and Remote Access Service (RRAS), administrators may encounter a scenario in which a client can establish a VPN connection using SSTP successfully, but is then disconnected immediately. The system event log contains an entry with Event ID 6 from the RasSstp source that includes the following error message.

“The SSTP-based VPN connection to the remote access server was terminated because of a security check failure. Security settings on the remote access server do not match settings on this computer. Contact the system administrator of the remote access server and relay the following information.”

Always On VPN Connect and Disconnect with SSTP

Common Causes

The two most common causes of this issue are when SSTP is configured for SSL offload, and when a VPN client is on a network where SSL inspection is taking place.

SSTP Offload

The most common cause of this issue is when SSL offload is configured for SSTP on an external load balancer or application delivery controller (ADC). To prevent interception from a Man-in-the-Middle attack, the VPN client sends the certificate hash of the SSL certificate used when the VPN connection was established. If this information does not match what is configured on the RRAS server, the connection is assumed to be compromised and the connection is immediately dropped.

SSL Inspection

Another scenario where this issue may occur is when a VPN client is behind a network device configured to perform SSL deep-packet inspection (DPI). SSTP VPN clients will be unable to connect to the VPN server in this scenario.

Resolution

When offloading SSL to another device, the RRAS server must be configured to know which SSL certificate is being presented to remote clients. This information is stored in the following registry key.

HKLM:\SYSTEM\CurrentControlSet\Services\SstpSvc\Parameters\SHA256CertificateHash

However, this registry entry requires a binary value, which makes it a challenge to configure manually. To resolve this problem, it is recommended that the same SSL certificate installed on the load balancer/ADC also be installed on the VPN server (even though SSL will be offloaded). To do this, first import the SSL certificate and private key in to the Local Computer certificate store, then open the RRAS management console and perform the following steps.

  1. Right-click the VPN server and choose Properties.
  2. Select the Security tab.
  3. Uncheck Use HTTP in the SSL Certificate Binding section.
  4. Select the appropriate SSL certificate from the Certificate drop-down list (click View to verify).
  5. Click Apply.

This will add the correct SSL certificate information to the registry. Next, re-enable HTTP for SSL offload by performing the following steps.

  1. Check Use HTTP in the SSL Certificate Binding section.
  2. Click Apply.

PowerShell Configuration

If the SSL certificate cannot be installed on the VPN server, or to automate this configuration across multiple servers remotely, download and run the Enable-SstpOffload PowerShell script from my GitHub repository here and run the following command.

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

For example…

Enable-SSTPOffload -CertificateHash “C3AB8FF13720E8AD9047DD39466B3C8974E592C2FA383D4A3960714CAEF0C4F2” -Restart

Additional Information

Windows 10 Always On VPN Load Balancing and SSL Offload

Windows 10 Always On VPN SSL Certificate Requirements for SSTP

Windows 10 Always On VPN Protocol Recommendations for Windows Server RRAS

Always On VPN SSTP Load Balancing and SSL Offload

SSL Certificate Considerations for DirectAccess IP-HTTPSThe Windows Server Routing and Remote Access Service (RRAS) is a popular choice for a VPN server to support Windows 10 Always On VPN deployments. One significant advantage RRAS provides is support for the Secure Socket Tunneling Protocol (SSTP). SSTP is a Microsoft proprietary VPN protocol that uses Transport Layer Security (TLS) to ensure privacy between the VPN client and server. The advantage to using a TLS-based transport is that it leverages the standard HTTPS TCP port 443, making it firewall friendly and ensuring ubiquitous remote access even behind highly restrictive firewalls.

Load Balancing SSTP

Load balancing SSTP can be accomplished in much the same way as a load balancing a common web server using HTTPS. The external load balancer is configured with a virtual IP address (VIP) and each VPN server is configured behind it. Session persistence should be configured to use SSL with source IP address persistence as a fallback.

SSL Offload for SSTP

In most cases, simply forwarding encrypted SSTP connections to the VPN server will be sufficient. However, offloading SSL/TLS processing to an Application Delivery Controller (ADC) or load balancer can be beneficial for the following reasons.

Resource Utilization

Enabling TLS offload for SSTP VPN connections can reduce CPU and memory utilization on the VPN server. However, this will likely only be necessary for very busy servers supporting many concurrent connections.

Security

In some cases, the administrator may not be able to install the public SSL certificate on the VPN server. For example, a security policy may exist that restricts SSL certificate installation to dedicated security devices using a Hardware Security Module (HSM). In some cases, it may be desirable to restrict access to high value certificates such as wildcard certificates.

Certificate Management

Often SSL certificates are implemented on load balancers to reduce certificate sprawl and to ease the management and administration burden in the enterprise. By having all enterprise certificates installed only on dedicated security devices, administrators can more effectively monitor and manage SSL certificate lifecycles.

SSTP Configuration for TLS Offload

Configuration changes must be made on the load balancer and the RRAS server to support TLS offload for SSTP.

Load Balancer

Install the public SSL certificate on the load balancer and configure it for TLS termination. Configure the load balancer to then use HTTP for backend server connections. Consult the load balancer vendor’s documentation for configuration guidance.

RRAS Server

If the public SSL certificate is installed on the VPN server, enabling TLS offload for SSTP is simple and straightforward. Follow the steps below to enable TLS offload for SSTP VPN connections.

  1. Open the RRAS management console (rrasmgmt.msc).
  2. Right-click the VPN server and choose Properties.
  3. Select the Security tab.
  4. Check Use HTTP in the SSL Certificate Binding section.
  5. Click Ok and then Yes to restart the Remote Access service.

Always On VPN SSTP Load Balancing and SSL Offload

If the public SSL certificate is not or cannot be installed on the RRAS server, additional configuration will be required. Specifically, SSL offload for SSTP must be configured using the Enable-SSTPOffload PowerShell script, which can be downloaded here.

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

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

For example…

Enable-SSTPOffload -CertificateHash “C3AB8FF13720E8AD9047DD39466B3C8974E592C2FA383D4A3960714CAEF0C4F2” -Restart

Re-Encryption

When offloading TLS for SSTP VPN connections, all traffic between the load balancer and the VPN server will be sent in the clear using HTTP. In some scenarios, TLS offload is required only for traffic inspection, not performance gain. When terminating TLS on the load balancer and re-encrypting connections to the VPN server is required, it is only supported if the same certificate is used on both the load balancer and the VPN server.

Additional Information

Windows 10 Always On VPN SSL Certificate Requirements for SSTP

Windows 10 Always On VPN IKEv2 and SSTP Fallback

Windows 10 Always On VPN Hands-On Training Classes for 2019

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