When configuring a Windows Server with the Routing and Remote Access Service (RRAS) role to support Windows 10 Always On VPN connections, the administrator may encounter the following error message when installing or updating the TLS certificate used for Secure Socket Tunneling Protocol (SSTP) connections.
“The thumbprint (cert hash) of the certificate used for Secure Socket Tunneling Protocol (SSTP) is different than the certificate bound to the Web listener (HTTP.sys). Configure SSTP to use the default certificate or the certificate bound to SSL. You can configure web server applications to use the same certificate used by SSTP.”
IIS Binding
Most commonly this error can occur if an administrator mistakenly binds a TLS certificate directly in IIS. To resolve this problem, open the IIS management console (inetmgr.exe), navigate to the Default Web Site and click Bindings in the Actions section. Highlight the HTTPS binding and click Remove. Once complete, open an elevated command window and run the iisreset.exe command.
Netsh
In some instances, the administrator may find no certificate bindings in the IIS management console. However, a certificate binding may still be present. To confirm, open an elevated command window and run the following command.
netsh.exe http show sslcert
Remove existing certificate binding by running the following commands.
netsh.exe http delete sslcert ipport=0.0.0.0:443
netsh.exe http delete sslcert ipport=[::]:443
SSTP Configuration
When configuring SSTP in RRAS for Always On VPN, certificate assignment should always be performed using the Routing and Remote Access management console (rrasmgmt.msc). No changes are required to be made in the IIS management console for SSTP.
Additional Information
Windows 10 Always On VPN SSL Certificate Requirements for SSTP
Windows 10 Always On VPN SSTP Load Balancing with Citrix NetScaler ADC Load Balancer
Windows 10 Always On VPN SSTP Load Balancing with Kemp LoadMaster Load Balancer
Windows 10 Always On VPN SSTP Load Balancing with F5 BIG-IP Load Balancer
During the planning phase of a Windows 10 Always On VPN implementation the administrator must decide between two tunneling options for VPN client traffic – split tunneling or force tunneling. When split tunneling is configured, only traffic for the on-premises network is routed over the VPN tunnel. Everything else is sent directly to the Internet. With force tunneling, all client traffic, including Internet traffic, is routed over the VPN tunnel. There’s been much discussion recently on this topic, and this article serves to outline the advantages and disadvantages for both tunneling methods.
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Always On VPN is infrastructure independent, which allows for many different deployment scenarios including on-premises and cloud-based. In Microsoft Azure, the Azure VPN gateway can be configured to support Windows 10 Always On VPN client connections in some scenarios. Recently I wrote about 
When configuring Windows 10 Always On VPN using Extensible Authentication Protocol (EAP), the administrator may encounter a scenario in which the client connection fails. The event log will include an event ID 20227 from the RasClient source that includes the following error message.
A Windows Server with the Network Device Enrollment Service (NDES) role can be provisioned on-premises to support certificate deployment for non-domain Windows 10 Always On VPN clients. In addition, the Microsoft Intune Connector must be installed and configured on the NDES server to allow Intune-managed clients to request and receive certificates from the on-premises Certification Authority (CA) server.
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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.
When 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.
Important! Updated April 29, 2020 to resolve an issue where the DirectAccess RADIUS encryption certificate was not published to the DirectAccess Server Settings GPO in Active Directory.
