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 SSTP Load Balancing with F5 BIG-IP

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.

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

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 SSL Load Balancing with F5 BIG-IP

Windows 10 Always On VPN IKEv2 and SSTP Fallback

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

DirectAccess Network Connectivity Assistant (NCA) Configuration Guidance

DirectAccess Network Connectivity Assistant (NCA) Configuration GuidanceThe DirectAccess Network Connectivity Assistant (NCA), first introduced in Windows 8, provides DirectAccess connectivity status information as well as diagnostic support on the client. The NCA validates that DirectAccess is working end-to-end by attempting to reach internal resources defined by the administrator during the configuration of DirectAccess. NCA configuration and operation is a source of much confusion. This article serves to provide best practice configuration guidance for the NCA to ensure optimum and reliable operation.

NCA Operation

When a DirectAccess client is outside the corporate network, it will attempt to establish a DirectAccess connection any time it has an active Internet connection. After a DirectAccess connection is made, the NCA will attempt to validate DirectAccess connectivity by verifying availability of corporate resources as defined in the DirectAccess configuration (Remote Access Management console, Step 1, Edit, Network Connectivity Assistant).

If the NCA can reach the defined internal corporate resource(s), the DirectAccess connection is verified end-to-end and it will report the connection status as “Connected”. If it fails to connect to any internal corporate resource, it displays “Connecting”.

DirectAccess Network Connectivity Assistant (NCA) Configuration Guidance

Figure 1. NCA successfully validated internal corporate resource connectivity.

DirectAccess Network Connectivity Assistant (NCA) Configuration Guidance

Figure 2. NCA failed to connect to one or more corporate resources.

NCA Configuration

When first installing DirectAccess, the Remote Access Setup wizard will collect information to be used by the NCA, including corporate resources, helpdesk email address, and DirectAccess connection name. It will also provide the option to allow DirectAccess clients to use local name resolution.

Note: The NCA settings configured in the Remote Access Management console pertain only to Windows 8.x and Windows 10 clients. They are not used by Windows 7 clients at all.

DirectAccess Network Connectivity Assistant (NCA) Configuration Guidance

Intuitively it would appear that information needs to be entered in the Resource and Type fields. However, it is recommended to leave this blank when first configuring DirectAccess. This is because the Remote Access Setup Wizard will automatically populate this field later. Specifying a resource during initial configuration will result in two entries being included, as shown here.

DirectAccess Network Connectivity Assistant (NCA) Configuration Guidance

As you can see, the Remote Access Setup wizard automatically added the resource directaccess-WebProbeHost.<internal domain.>. A corresponding DNS record is created that resolves this hostname to the internal IPv4 address of the DirectAccess server. In this configuration, the DirectAccess server itself serves as the corporate resource used by the NCA.

Multiple Corporate Resources

Having more than one resource to validate connectivity to the internal network is problematic though. If there are multiple entries specified, they must ALL pass a validation check from the client to report the connection status as “Connected”. Some administrators configure multiple entries with the mistaken belief that it will provide redundancy for the NCA, but it actually has the opposite effect. Having more than one entry only increases the chance of a false positive.

NCA Configuration Best Practices

It is recommended that only a single corporate resource URL be defined for the NCA. The default directaccess-WebProbeHost running on the DirectAccess server can be used, or, alternatively, another internal web server can be specified if desired. Any web server will work, including Microsoft Internet Information Services (IIS), Apache, NGINX, and most Application Delivery Controllers (ADCs) or load balancers. HTTPS is not required for the web probe host, only HTTP. If using an internal web server, ensure that it is highly available.

Do NOT use the Network Location Server (NLS) as a corporate resource! The NLS is exempted from the Name Resolution Policy Table (NRPT) on the client and is not reachable over DirectAccess. This will result in the NCA failing and reporting a “Connecting” status perpetually. In addition, avoid the use of PING for validating internal corporate resources. Ping uses ICMP which is inherently unreliable and commonly blocked by host and intermediary firewalls, making it an unreliable indicator of corporate network connectivity over DirectAccess.

Summary

The NCA is a crucial and often misunderstood component in the DirectAccess architecture. Follow the guidance outlined here to ensure that the NCA works reliably and effectively in your environment.

Additional Resources

DirectAccess Clients in Connecting State when using External Load Balancer
Planning and Implementing DirectAccess on Windows Server 2016 on Pluralsight
Implementing DirectAccess with Windows Server 2016 book