Always On VPN SSTP Certificate Binding Error

Always On VPN SSTP Certificate Binding ErrorWhen 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.”

Always On VPN SSTP Certificate Binding Error

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.

Always On VPN SSTP Certificate Binding Error

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

Always On VPN SSTP Certificate Binding Error

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

Always On VPN Split vs. Force Tunneling

Always On VPN Split vs. Force TunnelingDuring 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.

Force Tunneling

Force tunneling is typically enabled to meet the following requirements.

Visibility and Control

By routing all the client’s Internet traffic over the VPN tunnel, administrators can inspect, filter, and log Internet traffic using existing on-premises security solutions such as web proxies, content filters, or Next Generation Firewalls (NGFW).

Privacy

Enabling force tunneling ensures privacy and protection of all Internet communication. By routing all Internet traffic over the VPN, administrators can be certain that all communication from the Always On VPN client is encrypted, even when clients access unencrypted web sites or use untrusted or insecure wireless networks.

Force Tunneling Drawbacks

While configuring force tunneling for Always On VPN has some advantages, it comes with some serious limitations as well.

Poor User Experience

User experience is often degraded when all Internet traffic is routed over the VPN. These suboptimal network paths increase latency, and VPN encapsulation and encryption overhead increase fragmentation, leading to reduced throughput. Most Internet traffic is already encrypted in some form, and encrypting traffic that is already encrypted makes the problem even worse. In addition, force tunneling short-circuits geographic-based Content Delivery Networks (CDNs) further reducing Internet performance. Further, location-based services are often broken which can lead to improper default language selection or inaccurate web search results.

Increased Resource Consumption

Additional resources may need to be provisioned to support force tunneling. With corporate and Internet traffic coming over the VPN, more CPU, memory, and network resources may be required. Deploying additional VPN servers and higher throughput load balancers to support the increase in network traffic may also be necessary. Force tunneling also places higher demands on Internet Service Provider (ISP) links to the corporate datacenter.

Split Tunneling

The alternative to force tunneling is “split tunneling”. With split tunneling configured, only traffic destined for the internal corporate network is routed over the VPN. All other traffic is sent directly to the Internet. Administrators define IP networks that should be routed over the VPN, and those networks are added to the routing table on the VPN client.

Security Enforcement

The challenge of providing visibility and control of Internet traffic with split tunneling enabled can be met using a variety of third-party security solutions. Microsoft Defender ATP recently introduced support for web content filtering. Also, there are numerous cloud-based security offerings from many vendors that allow administrators to monitor and control client-based Internet traffic. Zscaler and Cisco Umbrella are two popular solutions, and no doubt there are many more to choose from.

Recommendations

The general guidance I provide customers is to use split tunneling whenever possible, as it provides the best user experience and reduces demands on existing on-premises infrastructure. Enabling split or force tunneling is ultimately a design decision that must be made during the planning phase of an Always On VPN implementation project. Both configurations are supported, and they each have their merits.

In today’s world, with many applications accessible via public interfaces, force tunneling is an antiquated method for providing visibility and control for managed devices in the field. If required, investigate the use of Microsoft or other third-party solutions that enforce security policy in place without the requirement to backhaul client Internet traffic to the datacenter over VPN for inspection, logging, and filtering.

Additional Information

Whitepaper: Enhancing VPN Performance at Microsoft

Whitepaper: How Microsoft Is Keeping Its Remote Workforce Connected

Microsoft Defender ATP Web Content Filtering

Always On VPN Device Tunnel Only Deployment Considerations

Always On VPN Device Tunnel Only Deployment ConsiderationsRecently I wrote about Windows Always On VPN device tunnel operation and best practices, explaining its common uses cases and requirements, as well as sharing some detailed information about authentication, deployment recommendations, and best practices. I’m commonly asked if deploying Always On VPN using the device tunnel exclusively, as opposed to using it to supplement the user tunnel, is supported or recommended. I’ll address those topics in detail here.

Device Tunnel Only?

To start, yes, it is possible to deploy Windows Always On VPN using only the device tunnel. In this scenario the administrator will configure full access to the network instead of limited access to domain infrastructure services and management servers.

Is It Recommended?

Generally, no. Remember, the device tunnel was designed with a specific purpose in mind, that being to provide pre-logon network connectivity to support scenarios such as logging on without cached credentials. Typically, the device tunnel is best used for its intended purpose, which is providing supplemental functionality to the user tunnel.

Deployment Considerations

The choice to implement Always On VPN using only the device tunnel is an interesting one. There are some potential advantages to this deployment model, but it is not without some serious limitations. Below I’ve listed some of the advantages and disadvantages to deploying the device tunnel alone for Windows 10 Always On VPN.

Advantages

Using the device tunnel alone does have some compelling advantages over the standard two tunnel (device tunnel/user tunnel) deployment model. Consider the following.

  • Single VPN Connection – Deploying the device tunnel alone means a single VPN connection to configure, deploy, and manage on the client. This also results in less concurrent connections and, importantly, less IP addresses to allocate and provision.
  • Reduced Infrastructure – The device tunnel is authenticated using only the device certificate. This certificate check is performed directly on the Windows Server Routing and Remote Access Service (RRAS) VPN server, eliminating the requirement to deploy Network Policy Server (NPS) servers for authentication.
  • User Transparency – The device tunnel does not appear in the modern Windows UI. The user will not see this connection if they click on the network icon in the notification area. In addition, they will not see the device tunnel connection in the settings app under Network & Internet > VPN. This prevents casual users from playing with the connection settings, and potentially deleting the connection entirely. It’s not that they can’t delete the device tunnel however, it’s just not as obvious.
  • Simplified Deployment – Deploying the device tunnel is less complicated than deploying the user tunnel. The device tunnel is provisioned once to the device and available to all users. This eliminates the complexity of having to deploy the user tunnel in each individual user’s profile.

Disadvantages

While there are some advantages to using the device tunnel by itself, this configuration is not without some serious limitations. Consider the following.

  • IKEv2 Only – The device tunnel uses the IKEv2 VPN protocol exclusively. It does not support SSTP. While IKEv2 is an excellent protocol in terms of security, it is commonly blocked by firewalls. This will prevent some users from accessing the network remotely depending on their location.
  • Limited OS Support – The device tunnel is only supported on Windows Enterprise edition clients, and those clients must be joined to a domain. Arguably the device tunnel wouldn’t be necessary if the client isn’t domain joined, but some organizations have widely deployed Windows Professional, which would preclude them from being able to use the device tunnel.
  • Machine Certificate Authentication Only – The device tunnel is authenticated using only the certificate issued to the device. This means anyone who logs on to the device will have full access to the internal network. This may or may not be desirable, depending on individual requirements.
  • No Mutual Authentication – When the device tunnel is authenticated, the server performs authentication of the client, but the client does not authenticate the server. The lack of mutual authentication increases the risk of a man-in-the-middle attack.
  • CRL Checks Not Enforced – By default, RRAS does not perform certificate revocation checking for device tunnel connections. This means simply revoking a certificate won’t prevent the device from connecting. You’ll have to import the client’s device certificate into the Untrusted Certificates certificate store on each VPN server. Fortunately, there is a fix available to address this limitation, but it involves some additional configuration. See Always On VPN Device Tunnel and Certificate Revocation for more details.
  • No Support for Azure Conditional Access – Azure Conditional Access requires EAP authentication. However, the device tunnel does not use EAP but instead uses a simple device certificate check to authenticate the device.
  • No Support for Multifactor Authentication – As the device tunnel is authenticated by the RRAS VPN server directly and authentication requests are not sent to the NPS server, it is not possible to integrate MFA with the device tunnel.
  • Limited Connection Visibility – Since the device tunnel is designed for the device and not the user it does not appear in the list of active network connections in the Windows UI. There is no user-friendly connection status indicator, although the connection can be viewed using the classic network control panel applet (ncpa.cpl).

Summary

The choice to deploy Windows Always On VPN using the device tunnel alone, or in conjunction with the user tunnel, is a design choice that administrators must make based on their individual requirements. Using the device tunnel alone is supported and works but has some serious drawbacks and limitations. The best experience will be found using the device tunnel as it was intended, as an optional component to provide pre-logon connectivity for an existing Always On VPN user tunnel.

Additional Information

Windows 10 Always On VPN Device Tunnel with Azure VPN Gateway

Windows 10 Always On VPN Device Tunnel and Certificate Revocation

Windows 10 Always On VPN Device Tunnel Configuration with Microsoft Intune

Windows 10 Always On VPN Device Tunnel Does Not Connect Automatically

Windows 10 Always On VPN Device Tunnel Missing in Windows 10 UI

Deleting a Windows 10 Always On VPN Device Tunnel

Windows 10 Always On VPN Device Tunnel Configuration using PowerShell

Windows 10 Always On VPN IKEv2 Features and Limitations