Always On VPN Fails with Windows 10 2004 Build 610

Updated 11/10/2020: Microsoft update KB4586781 has resolved the connectivity issues described in this post. If you had previously installed update KB4580364, please update to KB4586781 immediately.

A recent preview update for Windows 10 2004 has broken Always On VPN. Specifically, after installing the latest Preview update for Windows 10 2004 (KB4580364), Always On VPN connections will fail to connect automatically. They can be established manually, however.

Affected Builds

This issue affects Windows 10 2004 with build 19041.610 and 19042.610.

Always On VPN Fails with Windows 10 2004

Workaround

The only workaround currently is to remove this update.

Caveat

Although this is a “preview” update and an optional installation, it is important to know that preview updates are released in the next “patch Tuesday” release. Administrators are advised to carefully consider delaying the implementation until additional testing has been completed.

Additional Information

October 29, 2020 – KB4580364 (OS Builds 19041.610 and 19042.610) Preview Update

Windows 10 Always On VPN Updates for Windows 10 2004

Always On VPN Updates for Windows 10 2004

Always On VPN Updates for Windows 10 2004Microsoft recently made available an update for Windows 10 2004 that includes many important fixes for outstanding issues with Windows 10 Always On VPN. KB4571744 (build 19041.488) addresses many challenges faced by Always On VPN administrators today, including the following.

TPM

This update addresses an issue that prevents hash signing from working correctly using the Microsoft Platform Crypto Provider for Trusted Platform Module (TPM). This issue can occur when administrators configure Always On VPN to use Protected Extensible Authentication Protocol (PEAP) with client certificate authentication using a FortiGate security device.

Sleep/Hibernate

This update also addresses issues with Windows 10 Always On VPN failing to automatically reconnect when resuming from sleep or hibernate. I’ve written about issues with Always On VPN and sleep/hibernate in the past. This is an issue that has plagued Always On VPN since its introduction, so let’s hope this finally provides some meaningful relief from this persistent problem.

Certificate Authentication

When both the Always On VPN device tunnel and user tunnel are provisioned to a Windows 10 clients, user tunnel connections may be authenticated using the machine certificate and not EAP/PEAP. This can result in connections that are not validated as intended, and allowing a user to bypass configured NPS policies, MFA requirements, or conditional access rules. This update includes a fix for this issue, restoring proper authentication for the user tunnel when the device tunnel is also provisioned.

Device and User Tunnel Coexistence

A bug that first appeared when Windows 10 2004 was introduced prevented a device tunnel and user tunnel Always On VPN connection from being established to the same VPN server if the user tunnel used Internet Key Exchange Version 2 (IKEv2). This update restores full functionality under those conditions.

Update KB4571744

To resolve these issues with Windows 10 Always On VPN as well as others, download and install update KB4571744 today. If you are experiencing any of these issues with releases of Windows 10 prior to 2004, look for updates for those build to come later this year.

Additional Information

September 3, 2020 – KB4571744 (OS Build 19041.488) Preview

Windows 10 Always On VPN Connection Issues after Sleep or Hibernate

Windows 10 Always On VPN Bug in Windows 10 2004

Always On VPN Device Tunnel Operation and Best Practices

Always On VPN Device Tunnel Operation and Best PracticesUnlike DirectAccess, Windows 10 Always On VPN settings are deployed to the individual user, not the device. As such, there is no support for logging on without cached credentials using the default configuration. To address this limitation, and to provide feature parity with DirectAccess, Microsoft later introduced the device tunnel option in Windows 10 1709.

Device Tunnel Use Cases

The device tunnel is designed to allow the client device to establish an Always On VPN connection before the user logs on. This enables important scenarios such as logging on without cached credentials. This feature is crucial for organizations who expect users to log on to devices the first time remotely. The device tunnel can also be helpful for remote support, allowing administrators to manage remotely connected Always On VPN clients without having a user logged on. In addition, the device tunnel can alleviate some of the pain caused by administrators resetting remote worker’s passwords, or by users initiating a Self-Service Password Reset (SSPR).

Device Tunnel Requirements

The device tunnel requires Windows 10 Enterprise edition 1709 or later, and the client device must be joined to the domain. The device tunnel must be provisioned in the context of the local system account. Guidance for configuring and deploying a Windows 10 Always On VPN device tunnel can be found here.

Device Tunnel Authentication

The device tunnel is authenticated using a certificate issued to the client device, much the same as DirectAccess does. Authentication takes place on the Routing and Remote Access Service (RRAS) VPN server. It does not require a Network Policy Server (NPS) to perform authentication for the device tunnel.

Always On VPN Device Tunnel Operation and Best Practices

CRL Checking

Eventually an administrator may need to deny access to a device configured with an Always On VPN device tunnel connection. In theory, revoking the client device’s certificate and terminating their IPsec Security Associations (SAs) on the VPN server would accomplish this. However, Windows Server RRAS does not perform certificate revocation checking for Windows 10 Always On VPN device tunnel connections by default. Thankfully an update is available to enable this functionality. See Always On VPN Device Tunnel and Certificate Revocation for more details.

Configuration Best Practices

As the device tunnel is designed only to support domain authentication for remote clients, it should be configured with limited access to the on-premises infrastructure. Below is a list of required and optional infrastructure services that should be reachable over the device tunnel connection.

Required

  • All domain controllers
  • Enterprise DNS servers (if DNS is running on servers other than domain controllers)

Optional

  • All issuing certification authority (CA) servers
  • All certificate services online HTTP responders
  • All certificate services Online Certificate Status Protocol (OCSP) servers
  • System Center Configuration Manager (SCCM) distribution point servers
  • Windows Server Update Services (WSUS) servers
  • Management workstations

Limiting Access

Limiting access over the Always On VPN device tunnel can be accomplished in one of the following two ways.

Traffic Filters

The administrator can configure traffic filters on the device tunnel to restrict access only to those IP addresses required. However, be advised that when a traffic filter is enabled on the device tunnel, all inbound access will be blocked. This effectively prevents any remote management of the device from an on-premises system over the device tunnel.

Host Routes

An alternative to using traffic filters to limit access over the device tunnel is using host routes. Host routes are configured with a /32 prefix size and define a route to a specific individual host. The following is an example of host route configuration in ProfileXML.

Always On VPN Device Tunnel Operation and Best Practices

Note: A PowerShell script that enumerates all enterprise domain controllers and outputs their IP addresses in XML format for use in ProfileXML can be found here.

Caveats

Some organizations may have hundreds or even thousands of domain controllers, so creating individual host route entries for all domain controllers in profileXML may not be practical. In this scenario it is recommended to add host routes only for the domain controllers that belong to the Active Directory site where the VPN server resides.

Supportability

Do not use the <DomainNameInformation> element in ProfileXML or enable force tunneling for the device tunnel. Neither of these configurations are supported.

Tunnel Coexistence

The device tunnel can be safely deployed in conjunction with the user tunnel whenever its functionality is required.

DNS Registration

If the device tunnel and user tunnel are both deployed, it is recommended that only one of the tunnels be configured to register in DNS. If the device tunnel is configured to register its IP address in DNS, be advised that only those devices with routes configured in the device tunnel VPN profile will be able to connect remotely to Always On VPN clients.

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

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