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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

 

8 Comments
by Richard M. Hicks on March 4, 2019  •  Permalink
Posted in Always On VPN, AOVPN, application delivery controller, certificates, Encryption, enterprise mobility, GitHub, IP-HTTPS, Load Balancing, Mobility, PKI, PowerShell, public key infrastructure, Remote Access, routing and remote access service, RRAS, Security, SSL, SSL and TLS, SSTP, TLS, troubleshooting, VPN, Windows 10, Windows Server 2012, Windows Server 2012 R2, Windows Server 2016, Windows Server 2019
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Posted by Richard M. Hicks on March 4, 2019

https://directaccess.richardhicks.com/2019/03/04/always-on-vpn-sstp-connects-then-disconnects/

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

9 Comments
by Richard M. Hicks on February 18, 2019  •  Permalink
Posted in ADC, Always On VPN, AOVPN, application delivery controller, certificates, Encryption, enterprise mobility, High Availability, Load Balancing, Mobility, PowerShell, public key infrastructure, Remote Access, routing and remote access service, RRAS, Security, SSL, SSL and TLS, SSTP, TLS, VPN, Windows 10, Windows Server 2012, Windows Server 2012 R2, Windows Server 2016, Windows Server 2019
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Posted by Richard M. Hicks on February 18, 2019

https://directaccess.richardhicks.com/2019/02/18/always-on-vpn-sstp-load-balancing-and-ssl-offload/

Troubleshooting Always On VPN Error Code 809

When testing an Always On VPN connection, the administrator may encounter a scenario where the VPN client fails to connect to the VPN server. On the Windows 10 client the error message states the following.

“Can’t connect to [connection name]. The network connection between your computer and the VPN server could not be established because the remote server is not responding. This could be because one of the network devices (e.g. firewalls, NAT, routers, etc.) between your computer and the remote server is not configured to allow VPN connections. Please contact your Administrator or your service provider to determine which device may be causing the problem.”

Always On VPN and IKEv2 Fragmentation

In addition, the Application event log records an error message with Event ID 20227 from the RasClient source. The error message states the following.

“The User [username] dialed a connection named [connection name] with has failed. The error code returned on failure is 809.”

Troubleshooting Always On VPN Error Code 809

Connection Timeout

The error code 809 indicates a VPN timeout, meaning the VPN server failed to respond. Often this is related directly to network connectivity, but sometimes other factors can come in to play.

Troubleshooting VPN Error Code 809

When troubleshooting VPN error code 809 the following items should be carefully checked.

  • Name Resolution – Ensure the VPN server’s public hostname resolves to the correct IP address.
  • Firewall Configuration – Confirm the edge firewall is configured properly. Inbound TCP port 443 is required for the Secure Socket Tunneling Protocol (SSTP) and inbound UDP ports 500 and 4500 are required for the Internet Key Exchange version 2 (IKEv2) protocol. Make sure that any NAT rules are forwarding traffic to the correct server.
  • Load Balancer Configuration – If VPN servers are located behind a load balancer, make certain that virtual IP address and ports are configured correctly and that health checks are passing. For IKEv2 specifically, it is crucial that UDP ports 500 and 4500 be delivered to the same backend server. This commonly requires custom configuration. For example, on the KEMP LoadMaster the administrator will configure “port following”. On the F5 BIG-IP a  custom “persistence profile” must be configured. On the Citrix NetScaler a “persistency group” must be defined.

IKEv2 Fragmentation

VPN error code 809 can also be caused by IKE fragmentation when using the IKEv2 VPN protocol. During IKEv2 connection establishment, payload sizes may exceed the IP Maximum Transmission Unit (MTU) for the network path between the client and server. This causes the IP packets to be fragmented. However, it is not uncommon for intermediary devices (routers, NAT devices, or firewalls) to block IP fragments. When this occurs, a VPN connection cannot be established. However, looking at a network trace of the connection attempt, the administrator will see that the connection begins but subsequently fails.

Troubleshooting Always On VPN Error Code 809

Enable IKEv2 Fragmentation Support

The IKEv2 protocol includes support for fragmenting packets at the IKE layer. This eliminates the need for fragmenting packets at the IP layer. IKEv2 fragmentation must be configured on both the client and server.

Client

IKEv2 fragmentation was introduced in Windows 10 1803 and is enabled by default. No client-side configuration is required.

Server

IKEv2 is commonly supported on many firewall and VPN devices. Consult the vendor’s documentation for configuration guidance. For Windows Server Routing and Remote Access (RRAS) servers, IKEv2 fragmentation was introduced in Windows Server 1803 and is also supported in Windows Server 2019. It is enabled via a registry key. The following PowerShell command can be used to enable IKEv2 fragmentation on supported servers.

New-ItemProperty -Path “HKLM:\SYSTEM\CurrentControlSet\Services\RemoteAccess\Parameters\Ikev2\” -Name EnableServerFragmentation -PropertyType DWORD -Value 1 -Force

Validation

Once IKEv2 fragmentation is configured on the VPN server, a network capture will reveal the IKE_SA_INIT packet now includes the IKEV2_FRAGMENTATION_SUPPORTED notification message.

Always On VPN and IKEv2 Fragmentation

Additional Information

Windows 10 Always On VPN and IKEv2 Fragmentation

Windows 10 Always On VPN IKEv2 Security Configuration

Windows 10 Always On VPN Hands-On Training Classes

66 Comments
by Richard M. Hicks on February 14, 2019  •  Permalink
Posted in ADC, Always On VPN, AOVPN, application delivery controller, enterprise mobility, IKEv2, Load Balancing, Mobility, PowerShell, Remote Access, routing and remote access service, RRAS, Security, troubleshooting, VPN, Windows 10, Windows Server 2012 R2, Windows Server 2016, Windows Server 2019
Tagged , , , , , , , , , , , , , , , , , , , , , , , , , ,

Posted by Richard M. Hicks on February 14, 2019

https://directaccess.richardhicks.com/2019/02/14/troubleshooting-always-on-vpn-error-code-809/

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