Microsoft 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
Likely the single most common complaint about Windows 10 Always On VPN is that device tunnel or user tunnel VPN connections fail to reconnect automatically after a laptop computer wakes from sleep or hibernate. You will find many 
A longstanding issue with Windows 10 Always On VPN is that of VPN tunnel connectivity reliability and device tunnel/user tunnel interoperability. Many administrators have reported that Always On VPN connections fail to establish automatically at times, that only one tunnel comes up at a time (user tunnel or device tunnel, but not both), or that VPN tunnels fail to establish when coming out of sleep or hibernate modes. Have a look at the comments on this post and you’ll get a good understanding of the issues with Always On VPN.
