Always On VPN SSTP Certificate Binding Error

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 […]

Always On VPN Device Tunnel Operation and Best Practices

Unlike 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. […]

Always On VPN Updates for RRAS and IKEv2

Many users have reported connection stability issues using Windows Server 2019 Routing and Remote Access Service (RRAS) and the IKEv2 VPN protocol. Specifically, there have been reports of random disconnects for which the connection cannot be re-established for an extended period. At the same time, other VPN connections may work without issue. KB5003703 Microsoft has […]

Always On VPN Force Tunneling with Office 365 Exclusions

With the COVID-19 global pandemic forcing nearly everyone to work from home these days, organizations that implemented force tunneling for their VPN clients are likely encountering unexpected problems. When force tunneling is enabled, all client traffic, including Internet traffic, is routed over the VPN tunnel. This often overloads the VPN infrastructure and causes serious slowdowns, […]

DirectAccess Get-NetIPHttpsState Fails on Windows 10 1803

PowerShell is an essential tool for Windows administrators for configuration, task automation, monitoring, reporting, and problem resolution. When troubleshooting DirectAccess connectivity using the IP-HTTPS IPv6 transition technology, the Get-NetIPHttpsConfiguration and Get-NetIPHttpsState PowerShell commands are important for assessing the configuration and current state of the IP-HTTPS connection. When DirectAccess connectivity fails, these are some of the […]

Always On VPN Error Code 858

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. “The user [domain\username] dialed a connection named [connection name] which has failed. […]

Always On VPN Device Tunnel Only Deployment Considerations

Recently I wrote about Windows 10 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 […]

Always On VPN Device Tunnel Does Not Connect Automatically

When configuring a Windows 10 Always On VPN device tunnel, the administrator may encounter a scenario in which the device tunnel does not connect automatically. This can occur even when ProfileXML is configured with the AlwaysOn element set to “true”. Manual Connection An administrator can establish a device tunnel connection manually using rasdial.exe however, indicating […]

Always On VPN Device Tunnel Missing in Windows 10 UI

Unlike DirectAccess, Always On VPN connections are provisioned to the user, not the machine. Beginning with Windows 10 release 1709 Microsoft introduced the device tunnel option to provide feature parity with DirectAccess. The device tunnel provides pre-logon network connectivity to support important deployment scenarios such as logging on without cached credentials and unattended remote systems […]

Always On VPN Authentication Failure with Azure Conditional Access

Integrating Microsoft Azure Conditional Access with Windows 10 Always On VPN has several important benefits. The most important is that it allows administrators to improve their security posture by enforcing access polices that can be dynamically applied. For example, requiring multifactor authentication (MFA) for privileged users (e.g., administrators) or sign-ins that appear to be risky, […]

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