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 IKEv2 Connection Failure Error Code 800

Always On VPN administrators may encounter a scenario in which Windows 10 clients are unable to establish an IKEv2 VPN connection to a Windows Server Routing and Remote Access Service (RRAS) server or a third-party VPN device under the following conditions.

  1. The VPN connection is configured using ProfileXML.
  2. ProfileXML includes the <CryptographySuite> element.
  3. The VPN server is configured to use a custom IPsec policy.
  4. The VPN server supports only IKEv2.
  5. The <NativeProtocolType> in ProfileXML is set to Automatic.

When these specific conditions are met, the client will be unable to connect to the VPN server using IKEv2. The error message states:

The remote connection was not made because the attempted VPN tunnels failed. The VPN server might be unreachable. If this connection is attempting to use an L2TP/IPsec tunnel, the security parameters required for IPsec negotiation might not be configured properly.

Always On VPN IKEv2 VPN Connection Failure Error Code 800

In addition, the event log will include an error message from the RasClient source with event ID 20227 that includes the following error message.

The user [username] dialed a connection named [connection name] which has failed. The error code returned on failure is 800.

Always On VPN IKEv2 VPN Connection Failure Error Code 800

A manually configured VPN connection using IKEv2 will connect successfully under these same conditions, however.

IKEv2 Error Code 800

Error code 800 translates to ERROR_AUTOMATIC_VPN_FAILED, which is somewhat ambiguous. The error description is:

Unable to establish the VPN connection. The VPN server may be unreachable, or security parameters may not be configured properly for this connection.

Digging Deeper

A network trace of the IKEv2 VPN connection reveals the true source of the problem, which is a failure of the client and server to successfully negotiate an IKEv2 security association (SA). During the SA initiation process, the parameters offered by the client are unacceptable to the server, resulting in a NO_PROPOSAL_CHOSEN notification being returned by the server.

Always On VPN IKEv2 VPN Connection Failure Error Code 800

Custom Cryptography Settings Ignored

It appears that the Always On VPN connection ignores the custom cryptography settings defined in the CryptographySuite element in ProfileXML. However, this only occurs when the NativeProtocolType is set to Automatic. Presumably, this is a bug. 🙂

Workaround

As a workaround, set the NativeProtocolType to IKEv2. When NativeProtocolType is set to IKEv2, the VPN connection recognizes the IKEv2 parameters defined in the CryptographySuite element and the VPN connection will be established successfully.

Additional Information

Always On VPN IKEv2 Security Configuration

Always On VPN Certificate Requirements for IKEv2

Always On VPN IKEv2 Load Balancing with the KEMP LoadMaster Load Balancer

Always On VPN ECDSA SSL Certificate Request for SSTP

As I’ve discussed previously, it is strongly recommended that the TLS certificate used for SSTP be signed using the Elliptic Curve Digital Signature Algorithm (ECDSA). ECDSA provides better security and performance compared to RSA certificates for Windows 10 Always On VPN connections using SSTP. See my previous post Always On VPN SSL Certificate Requirements for SSTP for more information.

Certificate Signing Request

To generate a Certificate Signing Request (CSR) using ECDSA to send to a public Certification Authority (CA), open the local computer certificate store (certlm.msc) on any Windows server or client and follow the steps below.

  1. Expand Certificates – Local Computer.
  2. Right-click the Personal folder and choose All Tasks > Advanced Operations > Create Custom Request.
  3. Click Next.
  4. Select Proceed without enrollment policy.
  5. Click Next.
  6. From the Template drop-down list choose (No template) CNG key.
  7. Click Next.
  8. Click Details.Always On VPN ECDSA SSL Certificate Request for SSTP
  9. Click Properties.
  10. On the General tab enter a name in the Friendly name field.
  11. Click on the Subject tab.
    1. In the Subject name section, from the Type drop-down list choose Common name.
    2. In the Value field enter the VPN server’s public hostname and click Add.
    3. In the Alternative name section, from the Type drop-down list choose DNS.
    4. In the Value field enter the VPN server’s public hostname and click Add.Always On VPN ECDSA SSL Certificate Request for SSTP
  12. Click on the Extensions tab.
    1. Expand Extended Key Usage (application policies).
    2. Highlight Server Authentication.
    3. Click Add.Always On VPN ECDSA SSL Certificate Request for SSTP
  13. Click on the Private Key tab.
    1. Expand Cryptographic Service Provider.
    2. Uncheck RSA,Microsoft Software Key Storage Provider.
    3. Check ECDSA_P256,Microsoft Software Key Storage Provider.Always On VPN ECDSA SSL Certificate Request for SSTP
  14. Expand Key options.
    1. Select the option to Make private key exportable.Always On VPN ECDSA SSL Certificate Request for SSTP
  15. Click Ok.
  16. Click Next.
  17. Enter a name for the file in the File Name field.
  18. Click Finish.

Submit the Request

Once complete, submit the CSR for signing to your favorite public CA. Based on my experience, some CAs are easier to obtain ECDSA-signed certificates than other. Today, Digicert seems to be one of the better public CAs for obtaining EC TLS certificates.

Complete the Request

Once the CA has issued the certificate, import the certificate in to the local computer certificate store on the same client or server where the original CSR was created. The certificate can then be exported and imported on additional VPN servers, if required.

Additional Information

Always On VPN SSL Certificate Requirements for SSTP

Always On VPN Protocol Recommendations for RRAS

 

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