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.
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.
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.
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
The Windows Server 2016 Routing and Remote Access Service (RRAS) is commonly deployed as a VPN server for Windows 10 Always On VPN deployments. Using RRAS, Always On VPN administrators can take advantage of Microsoft’s proprietary 
